全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用：99美元
投递稿件

查看量下载量

相关文章

更多...

Organocatalysis: Key Trends in Green Synthetic Chemistry, Challenges, Scope towards Heterogenization, and Importance from Research and Industrial Point of View

DOI: 10.1155/2014/402860

Full-Text   Cite this paper   Add to My Lib

Abstract:

This paper purports to review catalysis, particularly the organocatalysis and its origin, key trends, challenges, examples, scope, and importance. The definition of organocatalyst corresponds to a low molecular weight organic molecule which in stoichiometric amounts catalyzes a chemical reaction. In this review, the use of the term heterogenized organocatalyst will be exclusively confined to a catalytic system containing an organic molecule immobilized onto some sort of support material and is responsible for accelerating a chemical reaction. Firstly, a brief description of the field is provided putting it in a green and sustainable perspective of chemistry. Next, research findings on the use of organocatalysts on various inorganic supports including nano(porous)materials, nanoparticles, silica, and zeolite/zeolitic materials are scrutinized in brief. Then future scope, research directions, and academic and industrial applications will be outlined. A succinct account will summarize some of the research and developments in the field. This review tries to bring many outstanding researches together and shows the vitality of the organocatalysis through several aspects. 1. Introduction In 1987, the United Nations Commission on Environment and Development (Brundtland Commission) [1] defined “sustainable development” as the development that meets the needs of the present without compromising the ability of future generations to meet their own needs. Two of the key aspects of sustainable development from an energy and chemical perspective are to develop more renewable forms of energy and to reduce pollution. Chemistry during the twentieth century changed the living standard of human beings. Among the greatest achievements of chemistry are petrochemical and pharmaceutical industries. But these industries are often blamed for polluting environment. The challenge for the present-day chemical industry is to continue providing applications and socioeconomic benefits in an environmentally friendly manner. Over the last few decades, green chemistry has been recognized as a culture and methodology for achieving sustainable development [2]. Green chemistry is chemistry able to promote innovative technologies that reduce or eliminate the use or generation of hazardous substances. Anastas and Warner defined the 12 principles of green chemistry (Figure 1) [3]. Catalysis (including enzyme catalysis, heterogeneous catalysis, and organocatalysis, in particular) is identified to be at the heart of greening of chemistry [4] because this branch of science is found to reduce the

 References

[1]  “Our Common Future: Report of the World Commission on Environment and Development, United Nations (UN) Commission on Environment and Development (Brundtland Commission), 1987,” Published as Annex to General Assembly document A/42/427, Development and International Co-operation: Environment, August 1987.
[2]  M. Lancaster, Green Chemistry: An Introductory Text, The Royal Society of Chemistry, Cambridge, UK, 2002.
[3]  P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, NY, USA, 1998.
[4]  J. H. Clark, “Catalysis for green chemistry,” Pure and Applied Chemistry, vol. 73, no. 1, pp. 103–111, 2001.
[5]  J. H. Clark and C. N. Rhodes, Clean Synthesis Using Porous Inorganic Solid Catalysts, RSC Clean Technology Monographs, Cambridge, UK, 2000.
[6]  W. Ostwald, “Die überwindung des wissenschaftlichen Materialismus,” in Verhandlungen der Gesellschaft Deutscher Naturforscher und ？rzte, pp. 155–168, 1895.
[7]  R. A. Sheldon, “Consider the environmental quotient,” Chemtech, vol. 25, pp. 38–47, 1994.
[8]  R. A. Sheldon and H. van Bekkum, Eds., Fine Chemicals Through Heterogeneous Catalysis, Wiley-VCH, Weinheim, Germany, 2001.
[9]  R. A. Sheldon and R. S. Downing, “Heterogeneous catalytic transformations for environmentally friendly production,” Applied Catalysis A, vol. 189, no. 2, pp. 163–183, 1999.
[10]  R. A. Sheldon, “The e factor: fifteen years on,” Green Chemistry, vol. 9, no. 12, pp. 1273–1283, 2007.
[11]  R. A. Sheldon, “E factors, green chemistry and catalysis: an odyssey,” Chemical Communications, no. 29, pp. 3352–3365, 2008.
[12]  R. A. Sheldon, “Selective catalytic synthesis of fine chemicals: opportunities and trends,” Journal of Molecular Catalysis A, vol. 107, no. 1–3, pp. 75–83, 1996.
[13]  R. A. Sheldon, “Catalysis and pollution prevention,” Chemistry & Industry, vol. 1, pp. 12–15, 1997.
[14]  R. A. Sheldon, “Catalysis: the key to waste minimization,” Journal of Chemical Technology and Biotechnology, vol. 68, pp. 381–388, 1997.
[15]  G. Ertl, H. Knozinger, and J. Weitkamp, Eds., Handbook of Heterogeneous Catalysis, Wiley-Vch, Weinheim, Germany, 1997.
[16]  R. A. van Santen, P. W. N. M. van Leeuwen, J. A. Moulijn, and B. A. Averill, Eds., Catalysis: An Intergrated Approach, Elsevier, Amsterdam, The Netherlands, 2nd edition, 1999.
[17]  J. R. Anderson and K. C. Pratt, Introduction To Characterisation and Testing of Catalysts, Academic Press, Sydney, Australia, 1985.
[18]  J. M. Walls and R. Smith, Eds., Surface Science Techniques, Pergamon, 1994.
[19]  J. W. Niemantsverdriet, Spectroscopy in Catalysis, Wiley-Vch, Weinheim, Germany, 2007.
[20]  J. J. Bozell and G. R. Petersen, “Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's “top 10” revisited,” Green Chemistry, vol. 12, no. 4, pp. 539–554, 2010.
[21]  R. A. Gross, M. Ganesh, and W. Lu, “Enzyme-catalysis breathes new life into polyester condensation polymerizations,” Trends in Biotechnology, vol. 28, no. 8, pp. 435–443, 2010.
[22]  C. J. Li and T. H. Chan, Organic Reactions in Aqueous Media, Wiley-VCH, New York, NY, USA, 1997.
[23]  P. A. Grieco, Organic Synthesis in Water, Kluwer Academic, Dordrecht, The Netherlands, 1997.
[24]  B. M. Trost, “Atom economy—a challenge for organic synthesis: homogeneous catalysis leads the way,” Angewandte Chemie International Edition, vol. 34, no. 3, pp. 259–281, 1995.
[25]  B. Cornils and W. A. Herrmann, in Applied Homogeneous Catalysis with Organometallic Compounds, B. Cornils and W. A. Herrmann, Eds., Wiley-VCH, Weinheim, Germany, 2nd edition, 2002.
[26]  B. Cornils and W. A. Herrmann, “Concepts in homogeneous catalysis: the industrial view,” Journal of Catalysis, vol. 216, no. 1-2, pp. 23–31, 2003.
[27]  S. Bhaduri and D. Mukesh, Homogeneous Catalysis, John Wiley & Sons, 2002.
[28]  G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, John Wiley & Sons, New York, NY, USA, 1992, Emphasis on Industrial Applications.
[29]  B. Cornils and W. A. Herrmann, Eds., Applied Homogeneous Catalysis by Organometallic Complexes, Verlag Chemie, Weinheim, Germany, 1996.
[30]  I. Ojima, Ed., Catalytic Asymmetric Synthesis, Verlag VCH, Weinheim, Germany, 1993.
[31]  R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, NY, USA, 1994.
[32]  H.-U. Blaser, A. Indolese, and A. Schnyder, “Applied homogeneous catalysis by organometallic complexes,” Current Science, vol. 78, no. 11, pp. 1336–1344, 2000.
[33]  M. Beller and H.-U. Blaser, Eds., Organometallics as Catalysts in the Fine Chemical Industry, vol. 42 of Topics in Organometallic Chemistry, Springer, 2012.
[34]  B. R. Cuenya, “Synthesis and catalytic properties of metal nanoparticles: size, shape, support, composition, and oxidation state effects,” Thin Solid Films, vol. 518, no. 12, pp. 3127–3150, 2010.
[35]  E. Victor Henrich and P. A. Cox, The Surface Science of Metal Oxides, Cambridge University Press, Cambridge, UK, 1994.
[36]  H. H. Kung, “Transition metal oxides,” in Surface Chemistry and Catalysis, Elsevier, Amsterdam, The Netherlands, 1989.
[37]  K. J. Klabunde, M. Fazlul Hoq, F. Mousah, and H. Matsuhashi, “Metal Oxides and their physico-chemical properties in Catalysis and Synthesis,” in Preparative Chemistry Using Supported Reagents, Academic Press, London, UK, 1987.
[38]  H. Sch？fer, Chemiker-Zeitung, vol. 101, no. 7/8, p. 325, 1977.
[39]  H.-C. Zhou, J. R. Long, and O. M. Yaghi, “Introduction to metal-organic frameworks,” Chemical Reviews, vol. 112, no. 2, pp. 673–674, 2012.
[40]  D. Farrusseng, Ed., Metal-Organic Frameworks. Applications From Catalysis to Gas Storage, Wiley-VCH, Weinheim, Germany, 2011.
[41]  N. Rahmat, A. Z. Abdullah, and A. R. Mohamed, “A review: mesoporous Santa Barbara amorphous-15, types, synthesis and its applications towards biorefinery production,” American Journal of Applied Sciences, vol. 7, no. 12, pp. 1579–1586, 2010.
[42]  S.-H. Wu, C.-Y. Mou, and H.-P. Lin, “Synthesis of mesoporous silica nanoparticles,” Chemical Society Reviews, vol. 42, pp. 3862–3875, 2013.
[43]  A. Bernardos and L. Kou？imská, “Applications of mesoporous silica materials in food: a review,” Czech Journal of Food Sciences, vol. 31, no. 2, pp. 99–107, 2013.
[44]  M. N. Timofeeva, V. N. Panchenko, Z. Hasan, and S.-H. Jhung, “Catalytic potential of the wonderful chameleons: nickel phosphate molecular sieves,” Applied Catalysis A, vol. 455, pp. 71–85, 2013.
[45]  I. R. Shaikh and S.-E. Park, “Microwave synthesis and catalytic applications of novel cobalt incorporated nickel phosphate,” Diffusion and Defect Data Pt.B: Solid State Phenomena, vol. 119, pp. 279–282, 2007.
[46]  I. R. Shaikh, Nanoporous nickel phosphate and silica materials for heterogeneous oxidation catalysis [Ph.D. thesis], Inha University, Inchon, Republic of Korea, 2007, Ph.D. thesis incomplete, unpublished and in conflict between S-E Park and Isak R. Shaikh.
[47]  Y. Tao, H. Kanoh, L. Abrams, and K. Kaneko, “Mesopore-modified zeolites: preparation, characterization, and applications,” Chemical Reviews, vol. 106, no. 3, pp. 896–910, 2006.
[48]  M. E. Davis, “Ordered porous materials for emerging applications,” Nature, vol. 417, no. 6891, pp. 813–821, 2002.
[49]  K. Tsuji, C. W. Jones, and M. E. Davis, “Organic-functionalized molecular sieves (OFMSs): I. Synthesis and characterization of OFMSs with polar functional groups,” Microporous and Mesoporous Materials, vol. 29, no. 3, pp. 339–349, 1999.
[50]  C. W. Jones, K. Tsuji, and M. E. Davis, “Organic-functionalized molecular sieves as shape-selective catalysts,” Nature, vol. 393, no. 6680, pp. 52–54, 1998.
[51]  M. E. Davis, “The quest for extra-large pore, crystalline molecular sieves,” Chemistry—A European Journal, vol. 3, pp. 1745–1750, 1997.
[52]  B. Notori, “Microporous crystalline titanium silicates,” Advances in Catalysis, vol. 41, pp. 253–334, 1996.
[53]  R. J. Saxon, “Crystalline microporous titanium silicates,” Topics in Catalysis, vol. 9, no. 1-2, pp. 43–57, 1999.
[54]  J. M. Thomas and R. Raja, “Design of a “green” one-step catalytic production of ε-caprolactam (precursor of nylon-6),” Proceedings of the National Academy of Sciences of the United States of America, vol. 102, no. 39, pp. 13732–13736, 2005.
[55]  M. Hartmann and L. Kevan, “Transition-metal ions in aluminophosphate and silicoaluminophosphate molecular sieves: location, interaction with adsorbates and catalytic properties,” Chemical Reviews, vol. 99, no. 3, pp. 635–663, 1999.
[56]  C. S. Cundy and P. A. Cox, “The hydrothermal synthesis of zeolites: history and development from the earliest days to the present time,” Chemical Reviews, vol. 103, no. 3, pp. 663–701, 2003.
[57]  A. Corma, “From microporous to mesoporous molecular sieve materials and their use in catalysis,” Chemical Reviews, vol. 97, no. 6, pp. 2373–2419, 1997.
[58]  G. De, M. Gusso, L. Tapfer et al., “Annealing behavior of silver, copper, and silver-copper nanoclusters in a silica matrix synthesized by the sol-gel technique,” Journal of Applied Physics, vol. 80, no. 12, pp. 6734–6739, 1996.
[59]  Y. Wan and D. Zhao, “On the controllable soft-templating approach to mesoporous silicates,” Chemical Reviews, vol. 107, no. 7, pp. 2821–2860, 2007.
[60]  A. K. Cheetham, G. Ferey, and T. Loiseau, Angewandte Chemie International Edition, vol. 38, p. 3298, 1999.
[61]  G. Ferey, “Microporous solids: from organically templated inorganic skeletons to hybrid frameworks . . . ecumenism in chemistry,” Chemistry of Materials, vol. 13, pp. 3084–3098, 2001.
[62]  C. N. R. Rao, S. Natarajan, and R. Vaidhyanathan, “Metal carboxylates with open architectures,” Angewandte Chemie International Edition, vol. 43, no. 12, pp. 1466–1496, 2004.
[63]  F. Schüth and W. Schmidt, “Microporous and mesoporous materials,” Advanced Materials, vol. 14, pp. 629–638, 2002.
[64]  F. Schuth, K. Sing, and J. Weitkamp, Eds., Handbook of Porous Solids, vol. I-V, Wiley-VCH, Weinheim, Germany, 2002.
[65]  Y. Wan and D. Y. Zhao, “On the controllable soft-templating approach to mesoporous silicates,” Chemical Reviews, vol. 107, no. 7, pp. 2821–2860, 2007.
[66]  V. Parvulescu, C. Anastasescu, and B. L. Su, “Bimetallic Ru-(Cr, Ni, or Cu) and La-(Co or Mn) incorporated MCM-41 molecular sieves as catalysts for oxidation of aromatic hydrocarbons,” Journal of Molecular Catalysis A, vol. 211, pp. 143–148, 2004.
[67]  S. Vetrivel and A. Pandurangan, “Co and Mn impregnated MCM-41: their applications to vapour phase oxidation of isopropylbenzene,” Journal of Molecular Catalysis A, vol. 227, pp. 269–278, 2005.
[68]  Y. Wan, D. Zhang, N. Hao, and D. Zhao, “Organic groups functionalised mesoporous silicates,” International Journal of Nanotechnology, vol. 4, p. 66, 2007.
[69]  V. Ayala, A. Corma, M. Iglesias, and F. Sanchez, “Mesoporous MCM41-heterogenised (salen)Mn and Cu complexes as effective catalysts for oxidation of sulfides to sulfoxides: isolation of a stable supported Mn(V)=O complex, responsible of the catalytic activity,” Journal of Molecular Catalysis A, vol. 221, pp. 201–208, 2004.
[70]  Z. G. Hajos and D. R. Parrish, “Asymmetric synthesis of bicyclic intermediates of natural product chemistry,” The Journal of Organic Chemistry, vol. 39, no. 12, pp. 1615–1621, 1974.
[71]  L. Shu and Y. Shi, “An efficient ketone-catalyzed epoxidation using hydrogen peroxide as oxidant,” The Journal of Organic Chemistry, vol. 65, pp. 8807–8810, 2000.
[72]  E. J. Corey, F. Xu, and M. C. Noe, “A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions,” Journal of the American Chemical Society, vol. 119, pp. 12414–12415, 1997.
[73]  B. Sellergren, R. N. Karmalkar, and K. J. Shea, “Enantioselective ester hydrolysis catalyzed by imprinted polymers. 2,” Journal of Organic Chemistry, vol. 65, no. 13, pp. 4009–4027, 2000.
[74]  J. von Liebig, “Ueber die Bildung des Oxamids aus Cyan,” Annalen der Chemie und Pharmacie, vol. 113, no. 2, pp. 246–247, 1860.
[75]  H. D. Dakin, “The catalytic action of amino-acids, peptones and proteins in effecting certain syntheses,” Journal of Biological Chemistry, vol. 7, p. 49, 1909.
[76]  W. Langenbeck, “über organische Katalysatoren. III. Die Bildung von Oxamid aus Dicyan bei Gegenwart von Aldehyden,” Justus Liebigs Annalen der Chemie, vol. 469, p. 16, 1929.
[77]  W. Langenbeck, Die Organische Katalysatoren und ihre Beziehungen zu den Fermenten, vol. 2, Springer, 1949.
[78]  W. Langenbeck, Fortschritte Der Chemischen Forschung, vol. 6, Springer, Berlin, Germany, 1966.
[79]  M. M. Vavon and P. Peignier, “L'application des alcalo？des dans la synthèse organique,” Bulletin de la Société Chimique de France, vol. 45, p. 293, 1929.
[80]  R. Wegler, “über die mit verschiedener Reaktionsgeschwindigkeit erfolgende Veresterung der optischen Antipoden eines Racemates durch opt. akt. Katalysatoren,” Justus Liebigs Annalen der Chemie, vol. 498, pp. 62–73, 1932.
[81]  S. Pizzarello and A. L. Weber, “Prebiotic amino acids as asymmetric catalysts,” Science, vol. 303, no. 5661, p. 1151, 2004.
[82]  G. Bredig and P. S. Fiske, Biochemische Zeitschrift, vol. 46, p. 7, 1912.
[83]  H. Pracejus, “Organische Katalysatoren, LXI. Asymmetrische Synthesen mit Ketenen, I. Alkaloid-katalysierte asymmetrische Synthesen von α-Phenyl-propions？ureestern,” Justus Liebigs Annalen der Chemie, vol. 634, pp. 9–22, 1960.
[84]  H. Pracejus, “Asymmetrische Synthesen mit Ketenen, II. Stereospezifische Addition von α-Phenyl-？thylamin an Phenyl-methyl-keten,” Justus Liebigs Annalen der Chemie, vol. 634, pp. 23–29, 1960.
[85]  S.-I. Yamada and G. Otani, “Asymmetric synthesis with amino acid II asymmetric synthesis of optically active 4,4-disubstituted-cyclohexenone,” Tetrahedron Letters, vol. 10, no. 48, pp. 4237–4240, 1969.
[86]  Z. G. Hajos and D. R. Parrish, German Patent DE, 2102623 1971.
[87]  Z. G. Hajos and D. R. Parrish, United States Patent US, 3975442, 1971.
[88]  U. Eder, G. Sauer, and R. Wiechert, “New type of asymmetric cyclization to optically active steroid CD partial structures,” Angewandte Chemie International Edition, vol. 10, pp. 496–497, 1971.
[89]  C. Allemann, R. Gordillo, F. R. Clemente, P. H.-Y. Cheong, and K. N. Houk, “Theory of asymmetric organocatalysis of aldol and related reactions: rationalizations and predictions,” Accounts of Chemical Research, vol. 37, no. 8, pp. 568–569, 2004.
[90]  H. Wynberg, “Asymmetric catalysis by alkaloids,” Topics in Stereochemistry, vol. 16, pp. 87–129, 1986.
[91]  H. Wynberg, “Catalytic asymmetric synthesis of chiral 4-substituted 2-oxetanones,” The Journal of Organic Chemistry, vol. 50, pp. 1977–1979, 1985.
[92]  H. Wynberg, “Asymmetric synthesis of (S)- and (R)-malic acid from ketene and chloral,” Journal of the American Chemical Society, vol. 104, pp. 166–168, 1982.
[93]  B. List, R. A. Lerner, and C. F. Barbas III, “Proline-catalyzed direct asymmetric aldol reactions,” Journal of the American Chemical Society, vol. 122, pp. 2395–2396, 2000.
[94]  T. Bui and C. F. Barbas III, “A proline-catalyzed asymmetric Robinson annulation reaction,” Tetrahedron Letters, vol. 41, no. 36, pp. 6951–6954, 2000.
[95]  R. B. Woodward, E. Logusch, K. P. Nambiar et al., “Asymmetric total synthesis of erythromcin. 1. Synthesis of an erythronolide A secoacid derivative via asymmetric induction,” Journal of the American Chemical Society, vol. 103, no. 11, pp. 3210–3213, 1981.
[96]  K. A. Ahrendt, C. J. Borths, and D. W. C. MacMillan, “New strategies for organic catalysis: the first highly enantioselective organocatalytic diels—Alder reaction,” Journal of the American Chemical Society, vol. 122, no. 17, pp. 4243–4244, 2000.
[97]  B. List, R. A. Lerner, and C. F. Barbas III, “Proline-catalyzed direct asymmetric aldol reactions,” Journal of the American Chemical Society, vol. 122, no. 10, pp. 2395–2396, 2000.
[98]  N. Vignola and B. List, “Catalytic asymmetric intramolecular α-alkylation of aldehydes,” Journal of the American Chemical Society, vol. 126, no. 2, pp. 450–451, 2004.
[99]  A. B. Northrup and D. W. C. MacMillan, “Two-step synthesis of carbohydrates by selective aldol reactions,” Science, vol. 305, no. 5691, pp. 1752–1755, 2004.
[100]  A. B. Northrup, I. K. Mangion, F. Hettche, and D. W. C. MacMillan, “Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: step one in a two-step synthesis of carbohydrates,” Angewandte Chemie International Edition, vol. 43, no. 16, pp. 2152–2154, 2004.
[101]  L. C. Dias, L. J. Steil, and V. D. A. Vasconcelos, “A short and efficient synthesis of (+)-prelactone B,” Tetrahedron Asymmetry, vol. 15, no. 1, pp. 147–150, 2004.
[102]  P. M. Pihko and A. Erkkil？, “Enantioselective synthesis of prelactone B using a proline-catalyzed crossed-aldol reaction,” Tetrahedron Letters, vol. 44, no. 41, pp. 7607–7609, 2003.
[103]  A. B. Northrup and D. W. C. MacMillan, “The first direct and enantioselective cross-aldol reaction of aldehydes,” Journal of the American Chemical Society, vol. 124, no. 24, pp. 6798–6799, 2002.
[104]  K. Sakthivel, W. Notz, T. Bui, and C. F. Barbas III, “Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions,” Journal of the American Chemical Society, vol. 123, no. 22, pp. 5260–5267, 2001.
[105]  B. List, P. Pojarliev, and C. Castello, “Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes,” Organic Letters, vol. 3, no. 4, pp. 573–575, 2001.
[106]  B. List, R. A. Lerner, and C. F. Barbas III, “Proline-catalyzed direct asymmetric aldol reactions,” Journal of the American Chemical Society, vol. 122, no. 10, pp. 2395–2396, 2000.
[107]  B. List, R. A. Lerner, and C. F. Barbas III, “Enantioselective aldol cyclodehydrations catalyzed by antibody 38C2,” Organic Letters, vol. 1, no. 1, pp. 59–61, 1999.
[108]  J. M. Betancort and C. F. Barbas III, “Direct asymmetric organocatalytic michael reactions of α,α-disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products,” Organic Letters, vol. 6, pp. 2527–2530, 2004.
[109]  A. Alexakis and O. Andrey, “Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene,” Organic Letters, vol. 4, no. 21, pp. 3611–3614, 2002.
[110]  B. List, P. Pojarliev, and H. J. Martin, “Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins,” Organic Letters, vol. 3, no. 16, pp. 2423–2425, 2001.
[111]  D. Enders and A. Seki, “Proline-catalyzed enantioselective Michael additions of ketones to nitrostyrene,” Synlett, no. 1, pp. 26–28, 2002.
[112]  J. M. Betancort and C. F. Barbas III, “Catalytic direct asymmetric Michael reactions: taming naked aldehyde donors,” Organic Letters, vol. 3, no. 23, pp. 3737–3740, 2001.
[113]  J. M. Betancort, K. Sakthivel, R. Thayumanavan, and C. F. Barbas III, “Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates,” Tetrahedron Letters, vol. 42, no. 27, pp. 4441–4444, 2001.
[114]  S. Hanessian and V. Pham, “Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones,” Organic Letters, vol. 2, no. 19, pp. 2975–2978, 2000.
[115]  M. Yamaguchi, Y. Igarashi, R. S. Reddy, T. Shiraishi, and M. Hirama, “Asymmetric Michael addition of nitroalkanes to prochiral acceptors catalyzed by proline rubidium salts,” Tetrahedron, vol. 53, no. 32, pp. 11223–11236, 1997.
[116]  N. S. Chowdari, J. T. Suri, and C. F. Barbas III, “Asymmetric synthesis of quaternary α-and β-amino acids and β-lactams via proline-catalyzed Mannich reactions with branched aldehyde donors,” Organic Letters, vol. 6, no. 15, pp. 2507–2510, 2004.
[117]  N. S. Chowdari, D. B. Ramachary, and C. F. Barbas III, “Organocatalysis in ionic liquids: highly efficient L-proline-catalyzed direct asymmetric Mannich reactions involving ketone and aldehyde nucleophiles,” Synlett, no. 12, pp. 1906–1909, 2003.
[118]  B. List, P. Pojarliev, W. T. Biller, and H. J. Martin, “The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols,” Journal of the American Chemical Society, vol. 124, no. 5, pp. 827–833, 2002.
[119]  A. Córdova, W. Notz, G. Zhong, J. M. Betancort, and C. F. Barbas III, “A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids,” Journal of the American Chemical Society, vol. 124, no. 9, pp. 1842–1843, 2002.
[120]  A. Córdova, S.-I. Watanabe, F. Tanaka, W. Notz, and C. F. Barbas III, “A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives,” Journal of the American Chemical Society, vol. 124, no. 9, pp. 1866–1867, 2002.
[121]  A. Corodova and C. F. Barbas III, “anti-Selective SMP-catalyzed direct asymmetric Mannich-type reactions: synthesis of functionalized amino acid derivatives,” Tetrahedron Letters, vol. 43, pp. 7749–7752, 2002.
[122]  B. List, “The direct catalytic asymmetric three-component Mannich reaction,” Journal of the American Chemical Society, vol. 122, no. 38, pp. 9336–9337, 2000.
[123]  F. Shi, W. Tan, R.-Y. Zhu, G.-J. Xing, and S.-J. Tu, “catalytic asymmetric five-component tandem reaction: diastereo- and enantioselective synthesis of densely functionalized tetrahydropyridines with biological importance,” Advanced Synthesis & Catalysis, vol. 355, no. 8, pp. 1605–1622, 2013.
[124]  J. W. Yang, M. T. Hechavarria Fonseca, and B. List, “Catalytic asymmetric reductive Michael cyclization,” Journal of the American Chemical Society, vol. 127, no. 43, pp. 15036–15037, 2005.
[125]  B. List, “Direct catalytic asymmetric α-amination of aldehydes,” Journal of the American Chemical Society, vol. 124, pp. 5656–5657, 2002.
[126]  G. Zhong, “A facile and rapid route to highly enantiopure 1,2-diols by novel catalytic asymmetric α-aminoxylation of aldehydes,” Angewandte Chemie International Edition, vol. 42, no. 35, pp. 4247–4250, 2003.
[127]  S. P. Brown, M. P. Brochu, C. J. Sinz, and D. W. C. MacMillan, “The direct and enantioselective organocatalytic α-oxidation of aldehydes,” Journal of the American Chemical Society, vol. 125, no. 36, pp. 10808–10809, 2003.
[128]  A. B？gevig, H. Sunden, and A. Córdova, “Direct catalytic enantioselective alpha-aminoxylation of ketones: a stereoselective synthesis of alpha-hydroxy and alpha,alpha'-dihydroxy ketones,” Angewandte Chemie International Edition, vol. 43, pp. 1109–1112, 2004.
[129]  J. Seayad and B. List, “Asymmetric organocatalysis,” Organic & Biomolecular Chemistry, vol. 3, pp. 719–724, 2005.
[130]  R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, and P. Melchiorre, “Proline-catalyzed asymmetric formal α-alkylation of aldehydes via vinylogous iminium ion intermediates generated from arylsulfonyl indoles,” Angewandte Chemie International Edition, vol. 47, no. 45, pp. 8707–8710, 2008.
[131]  R. K. Kunz and D. W. C. MacMillan, “Enantioselective organocatalytic cyclopropanations. The identification of a new class of iminium catalyst based upon directed electrostatic activation,” Journal of the American Chemical Society, vol. 127, no. 10, pp. 3240–3241, 2005.
[132]  J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kj？rsgaard, and K. A. J？rgensen, “A general organocatalyst for direct α-functionalization of aldehydes: stereoselective C？C, C？N, C？F, C？Br, and C？S bond-forming reactions. Scope and mechanistic insights,” Journal of the American Chemical Society, vol. 127, p. 18296, 2005.
[133]  A. B？gevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, and K. A. J？rgensen, “Direct organo-catalytic asymmetric α-amination of aldehydes—a simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids,” Angewandte Chemie International Edition, vol. 41, pp. 1790–1793, 2002.
[134]  M. Marigo and K. A. J？rgensen, “α-Heteroatom functionalization,” in Enantioselective Organocatalysis, P. I. Dalko, Ed., Chapter 2.2, Wiley-VCH, Weinheim, Germany, 2007.
[135]  M. Marigo, T. Schulte, J. Franzén, and K. A. J？rgensen, “Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes,” Journal of the American Chemical Society, vol. 127, pp. 15710–15711, 2005.
[136]  M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, and K. A. J？rgensen, “Asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes with hydrogen peroxide,” Journal of the American Chemical Society, vol. 127, pp. 6964–6965, 2005.
[137]  A. Carlone, G. Bartoli, M. Bosco, L. Sambri, and P. Melchiorre, “Organocatalytic asymmetric hydrophosphination of α,β-unsaturated aldehydes,” Angewandte Chemie International Edition, vol. 46, no. 24, pp. 4504–4506, 2007.
[138]  I. Ibrahem, R. Rios, J. Vesely et al., “Enantioselective organocatalytic hydrophosphination of α,β-unsaturated aldehydes,” Angewandte Chemie International Edition, vol. 46, no. 24, pp. 4507–4510, 2007.
[139]  X. Yu and W. Wang, “Organocatalysis: asymmetric cascade reactions catalysed by chiral secondary amines,” Organic & Biomolecular Chemistry, vol. 6, pp. 2037–2046, 2008.
[140]  D. Enders, M. R. M. Hüttl, C. Grondal, and G. Raabe, “Control of four stereocentres in a triple cascade organocatalytic reaction,” Nature, vol. 441, pp. 861–863, 2006.
[141]  A. E. Allen and D. W. C. MacMillan, “Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis,” Journal of the American Chemical Society, vol. 133, no. 12, pp. 4260–4263, 2011.
[142]  A. E. Allen and D. W. C. MacMillan, “The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective α-trifluoromethylation of aldehydes,” Journal of the American Chemical Society, vol. 132, no. 14, pp. 4986–4987, 2010.
[143]  H.-W. Shih, M. N. Vander Wal, R. L. Grange, and D. W. C. MacMillan, “Enantioselective α-benzylation of aldehydes via photoredox organocatalysis,” Journal of the American Chemical Society, vol. 132, no. 39, pp. 13600–13603, 2010.
[144]  D. W. C. MacMillan, “The advent and development of organocatalysis,” Nature, vol. 455, no. 7211, pp. 304–308, 2008.
[145]  T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, and D. W. C. MacMillan, “Enantioselective organocatalysis using SOMO activation,” Science, vol. 316, no. 5824, pp. 582–585, 2007.
[146]  S. G. Ouellet, A. Walji, and D. W. C. MacMillan, “Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters,” Accounts of Chemical Research, vol. 40, pp. 1327–1339, 2007.
[147]  Y. Huang, A. M. Walji, C. H. Larsen, and D. W. C. MacMillan, “Enantioselective organo-cascade catalysis,” Journal of the American Chemical Society, vol. 127, no. 43, pp. 15051–15053, 2005.
[148]  S. P. Brown, M. P. Brochu, C. J. Sinz, and D. W. C. MacMillan, “The direct and enantioselective organocatalytic α-oxidation of aldehydes,” Journal of the American Chemical Society, vol. 125, no. 36, pp. 10808–10809, 2003.
[149]  N. A. Para and D. W. C. MacMillan, “New strategies in organic catalysis: the first enantioselective organocatalytic Friedel-Crafts alkylation,” Journal of the American Chemical Society, vol. 123, no. 18, pp. 4370–4371, 2001.
[150]  W. S. Jen, J. J. M. Wiener, and D. W. C. MacMillan, “New strategies for organic catalysis: the first enantioselective organocatalytic 1,3-dipolar cycloaddition,” Journal of the American Chemical Society, vol. 122, no. 40, pp. 9874–9875, 2000.
[151]  F. Calderón, R. Fernández, F. Sánchez, and A. Fernández-Mayoralas, “Asymmetric aldol reaction using immobilized proline on mesoporous support,” Advanced Synthesis & Catalysis, vol. 347, no. 10, pp. 1395–1403, 2005.
[152]  Z. An, W. Zhang, H. Shi, and J. He, “An effective heterogeneous l-proline catalyst for the asymmetric aldol reaction using anionic clays as intercalated support,” Journal of Catalysis, vol. 241, no. 2, pp. 319–327, 2006.
[153]  M. Gruttadauria, F. Giacalone, and R. Noto, “Supported proline and proline-derivatives as recyclable organocatalysts,” Chemical Society Reviews, vol. 37, no. 8, pp. 1666–1688, 2008.
[154]  O. Bortolini, A. Cavazzini, P. P. Giovannini et al., “A combined kinetic and thermodynamic approach for the interpretation of continuous-flow heterogeneous catalytic processes,” Chemistry—A European Journal, vol. 19, no. 24, pp. 7802–7808, 2013.
[155]  A. Berkessel and H. Groeger, Eds., Asymmetric Organocatalysis: From Biomimetic Concepts To Applications in Asymmetric SynthesisSpecial Issue: Asymmetric Organocatalysis, Wiley-VCH, Weinheim, Germany, 2005.
[156]  A. Berkessel and H. Groeger, Metal-Free Organic Catalysts in Asymmetric Synthesis, Wiley-VCH, Weinheim, Germany, 2004.
[157]  K. N. Houk and B. List, “Special issue: asymmetric organocatalysis,” Accounts of Chemical Research, vol. 37, no. 8, p. 487, 2004.
[158]  F. Xu, M. Zacuto, N. Yoshikawa et al., “Asymmetric synthesis of telcagepant, a CGRP receptor antagonist for the treatment of migraine,” Journal of Organic Chemistry, vol. 75, no. 22, pp. 7829–7841, 2010.
[159]  H. U. Blaser and E. Schmidt, “Introduction,” in Asymmetric Catalysis on Industrial Scale, H. U. Blaser and E. Schmidt, Eds., pp. 1–19, Wiley-VCH, Weinheim, Germany, 2004.
[160]  H. U. Blaser, B. Pugin, and F. Spindler, “Progress in enantioselective catalysis assessed from an industrial point of view,” Journal of Molecular Catalysis A, vol. 231, pp. 1–20, 2005.
[161]  H. U. Blaser, “Enantioselective catalysis in fine chemicals production,” Chemical Communications, pp. 293–296, 2003.
[162]  S. S. V. Ramasastry, H. Zhang, F. Tanaka, and C. F. Barbas III, “Direct catalytic asymmetric synthesis of anti-1,2-amino alcohols and syn-1,2-diols through organocatalytic anti-Mannich and syn-aldol reactions,” Journal of the American Chemical Society, vol. 129, pp. 288–289, 2007.
[163]  Y. Zhao, J. Rodrigo, A. H. Hoveyda, and M. L. Snapper, “Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule,” Nature, vol. 443, no. 7107, pp. 67–70, 2006.
[164]  S. Saha and J. N. Moorthy, “Enantioselective organocatalytic Biginelli reaction: dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality,” The Journal of Organic Chemistry, vol. 76, pp. 396–402, 2011.
[165]  S. Gore, S. Baskaran, and B. Koenig, “Efficient synthesis of 3,4-dihydropyrimidin-2-ones in low melting tartaric acid-urea mixtures,” Green Chemistry, vol. 13, no. 4, pp. 1009–1013, 2011.
[166]  N. Li, X. H. Chen, J. Song, S. W. Luo, W. Fan, and L. Z. Gong, “Highly enantioselective organocatalytic Biginelli and Biginelli-like condensations: reversal of the stereochemistry by tuning the 3,3′-disubstituents of phosphoric acids,” Journal of the American Chemical Society, vol. 132, p. 10953, 2010.
[167]  N. Lu, D. Chen, G. Zhang, and Q. Liu, “Theoretical investigation on enantioselective Biginelli reaction catalyzed by natural tartaric acid,” International Journal of Quantum Chemistry, vol. 111, pp. 2031–2038, 2010.
[168]  M. Lei, “An efficient and environmentally friendly procedure for synthesis of pyrimidinone derivatives by use of a Biginelli-type reaction,” Monatshefte für Chemie, vol. 141, pp. 1005–1008, 2010.
[169]  Y. Y. Wu, Z. Chai, X. Y. Liu, G. Zhao, and S. W. Wang, “Synthesis of substituted 5-(Pyrrolidin-2-yl)tetrazoles and their application in the asymmetric Biginelli reaction,” European Journal of Organic Chemistry, vol. 6, pp. 904–911, 2009.
[170]  M. M. Savant, A. M. Pansuriya, C. V. Bhuva, N. P. Kapuriya, and Y. T. Naliapara, “Etidronic acid: a new and efficient catalyst for the synthesis of novel 5-nitro-3,4-dihydropyrimidin-2(1H)-ones,” Catalysis Letters, vol. 132, no. 1-2, pp. 281–284, 2009.
[171]  J. N. Sangshetti, N. D. Kokare, and D. B. Shinde, “Oxalic acid as a versatile catalyst for one pot facile synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their thione analogues,” Journal of Heterocyclic Chemistry, vol. 45, no. 4, pp. 1191–1194, 2008.
[172]  E. Ramu, V. Kotra, N. Bansal, R. Varala, and S. R. Adapa, “Green approach for the efficient synthesis of Biginelli compounds promoted by citric acid under solvent-free conditions,” Rasayan Journal of Chemistry, vol. 1, pp. 188–194, 2008.
[173]  D. B. Ramachary, N. S. Chowdari, and C. F. Barbas III, “Amine-catalyzed direct self Diels-Alder reactions of α,β-unsaturated ketones in water: synthesis of pro-chiral cyclohexanones,” Tetrahedron Letters, vol. 43, no. 38, pp. 6743–6746, 2002.
[174]  D. B. Ramachary, K. Anebouselvy, N. S. Chowdari, and C. F. Barbas III, “Direct organocatalytic asymmetric heterodomino reactions: the Knoevenagel/Diels-Alder/epimerization sequence for the highly diastereoselective synthesis of symmetrical and nonsymmetrical synthons of benzoannelated centropolyquinanes,” Journal of Organic Chemistry, vol. 69, no. 18, pp. 5838–5849, 2004.
[175]  R. Martín-Rapún, X. Fan, S. Sayalero, M. Bahramnejad, F. Cuevas, and M. A. Pericàs, “Highly active organocatalysts for asymmetric anti-mannich reactions,” Chemistry—A European Journal, vol. 17, no. 32, pp. 8780–8783, 2011.
[176]  T. Ooi, M. Taniguchi, M. Kameda, and K. Maruoka, “Direct asymmetric aldol reactions of glycine schiff base with aldehydes catalyzed by chiral quaternary ammonium salts,” Angewandte Chemie International Edition, vol. 41, pp. 4542–4544, 2002.
[177]  D. R. Burri, I. R. Shaikh, S.-C. Han, and S.-E. Park, “Facile heterogenization of homogeneous ferrocene catalyst on SBA-16,” Studies in Surface Science and Catalysis, vol. 165, pp. 647–650, 2007.
[178]  I. R. Shaikh, “Heterogenization of a basic ionic liquid bearing anion on mesoporous SBA-16 and its use as catalyst in knoevenagel reaction,” in Proceedings of the National Conference on Drug Designing and Discovery, pp. 81–85, Devchand College, Arjun Nagar, Ta. Kagal, District Kolhapur, India, September 2013, http://devchandcollege.org/e%20proceeding%203D13.html.
[179]  I. R. Shaikh and A. A. Shaikh, “Heterogenization of ionic liquid containing Hünig base on mesoporous SBA-16 and its use as catalyst in knovenagel condensation,” in Proceedings of the National Conference on Frontiers of Physical, Chemical and Biological Sciences (FPCBS '13), University of Pune, Ganeshkhind, Pune, India, October 2013, published as special issue in: Environment Observer, vol. 13, pp. 35-36, 2013, http://www.seeram.org/.
[180]  D. Petruzziello, M. Stenta, A. Mazzanti, and P. G. Cozzi, “A rational approach towards a new ferrocenyl pyrrolidine for stereoselective enamine catalysis,” Chemistry—A European Journal, vol. 19, no. 24, pp. 7696–7700, 2013.
[181]  S. Sulzer-Mossé and A. Alexakis, “Chiral amines as organocatalysts for asymmetric conjugate addition to nitroolefins and vinyl sulfonesviaenamine activation,” Chemical Communications, no. 30, pp. 3123–3135, 2007.
[182]  Z. An, W. Zhang, H. Shi, and J. He, “An effective heterogeneous l-proline catalyst for the asymmetric aldol reaction using anionic clays as intercalated support,” Journal of Catalysis, vol. 241, no. 2, pp. 319–327, 2006.
[183]  L. Albrecht, G. Dickmeiss, C. F. Weise, C. Rodríguez-Escrich, and K. A. J？rgensen, “Dienamine-mediated inverse-electron-demand hetero-diels-alder reaction by using an enantioselective H-bond-directing strategy,” Angewandte Chemie International Edition, vol. 51, no. 52, pp. 13109–13113, 2012.
[184]  Q. Ren and J. Wang, “Recent developments in amine-catalyzed non-asymmetric transformations,” Asian Journal of Organic Chemistry, vol. 2, no. 7, pp. 542–557, 2013.
[185]  T. Li, J. Zhu, D. Wu et al., “A strategy enabling enantioselective direct conjugate addition of inert aryl methane nucleophiles to enals with a chiral amine catalyst under mild conditions,” Chemistry—A European Journal, vol. 19, no. 28, pp. 9147–9150, 2013.
[186]  G. Talavera, E. Reyes, J. L. Vicario, and L. Carrillo, “Cooperative dienamine/hydrogen-bonding catalysis: enantioselective formal [2+2] cycloaddition of enals with nitroalkenes,” Angewandte Chemie International Edition, vol. 51, no. 17, pp. 4104–4107, 2012.
[187]  D. B. Ramachary and Y. V. Reddy, “Dienamine catalysis: an emerging technology in organic synthesis,” European Journal of Organic Chemistry, no. 5, pp. 868–887, 2012.
[188]  J. Chin, F. Mancin, N. Thavarajah, D. Lee, A. Lough, and D. S. Chung, “Controlling diaza-Cope rearrangement reactions with resonance-assisted hydrogen bonds,” Journal of the American Chemical Society, vol. 125, pp. 15276–15277, 2003.
[189]  H. J. Kim, H. Kim, G. Alhakimi et al., “Preorganization in highly enantioselective diaza-Cope rearrangement reaction,” Journal of the American Chemical Society, vol. 127, pp. 16370–16371, 2005.
[190]  H. J. Kim, W. Kim, A. J. Lough, B. M. Kim, and J. Chin, “A cobalt(III)-salen complex with an axial substituent in the diamine backbone: stereoselective recognition of amino alcohols,” Journal of the American Chemical Society, vol. 127, pp. 16776–16777, 2005.
[191]  L. Cui, Y. Zhu, S. Luo, and J.-P. Cheng, “Primary-tertiary diamine/br？nsted acid catalyzed C–C coupling between para-vinylanilines and aldehydes,” Chemistry—A European Journal, vol. 19, no. 29, pp. 9481–9484, 2013.
[192]  M. Orlandi, M. Benaglia, L. Raimondi, and G. Celentano, “2-Aminoimidazolyl and 2-aminopyridyl (S)-prolinamides as versatile multifunctional organic catalysts for aldol, Michael and Diels Alder reactions,” European Journal of Organic Chemistry, vol. 12, pp. 2346–2354, 2013.
[193]  H. Wang, Y. Wang, H. Song, Z. Zhou, and C. Tang, “Bifunctional squaramide-catalyzed one-pot sequential Michael addition/dearomative bromination: convenient access to optically active brominated pyrazol-5(4H)-ones with adjacent quaternary and tertiary stereocenters,” European Journal of Organic Chemistry, vol. 2013, no. 22, pp. 4844–4851, 2013.
[194]  B. Tan, G. Hernández-Torres, and C. F. Barbas III, “Rationally designed amide donors for organocatalytic asymmetric Michael reactions,” Angewandte Chemie International Edition, vol. 51, no. 22, pp. 5381–5385, 2012.
[195]  D. Nguyen, R. K. Akhani, C. I. Sheppard, and S. L. Wiskur, “Structure-activity relationship of formamides as organocatalysts: the significance of formamide structure and conformation,” European Journal of Organic Chemistry, vol. 12, pp. 2279–2283, 2013.
[196]  G. Lelais and D. W. C. MacMillan, “Modern strategies in organic catalysis: the advent and development of iminium activation,” Aldrichimica Acta, vol. 39, no. 3, pp. 79–87, 2006.
[197]  S. Lee and D. W. C. MacMillan, “Organocatalytic vinyl and Friedel-Crafts alkylations with trifluoroborate salts,” Journal of the American Chemical Society, vol. 129, no. 50, pp. 15438–15439, 2007.
[198]  N. A. Paras and D. W. C. MacMillan, “New strategies in organocatalysis:The first enantioselective organocatalytic Friedel-Crafts alkylation,” Journal of the American Chemical Society, vol. 123, pp. 4370–4371, 2001.
[199]  M. P. Brochu, S. P. Brown, and D. W. C. MacMillan, “Direct and enantioselective organocatalytic α-chlorination of aldehydes,” Journal of the American Chemical Society, vol. 126, no. 13, pp. 4108–4109, 2004.
[200]  T. D. Beeson and D. W. C. MacMillan, “Enantioselective organocatalytic α-fluorination of aldehydes,” Journal of the American Chemical Society, vol. 127, no. 24, pp. 8826–8828, 2005.
[201]  M. T. H. Fonseca and B. List, “Catalytic asymmetric intramolecular Michael reaction of aldehydes,” Angewandte Chemie International Edition, vol. 43, no. 30, pp. 3958–3960, 2004.
[202]  S. G. Ouellet, J. B. Tuttle, and D. W. MacMillan, “Enantioselective organocatalytic hydride reduction,” Journal of the American Chemical Society, vol. 127, pp. 32–33, 2005.
[203]  MacMillan Imidazolidinone OrganoCatalysts are a trademark of Materia, Inc., https://www.princeton.edu/chemistry/macmillan/publications/aldrichimica.pdf.
[204]  M. C. Holland, S. Paul, W. B. Schweizer et al., “Noncovalent interactions in organocatalysis: modulating conformational diversity and reactivity in the MacMillan catalyst,” Angewandte Chemie International Edition, vol. 52, no. 31, pp. 7967–7971, 2013.
[205]  G. Chollet, F. Rodriguez, and E. Schulz, “A new method for recycling asymmetric catalysts via formation of charge transfer complexes,” Organic Letters, vol. 8, pp. 539–542, 2006.
[206]  L. Xing, J. H. Xie, Y. S. Chen, L. X. Wang, and Q. L. Zhou, “Simply modified chiral diphosphine: catalyst recycling via non-covalent absorption on carbon nanotubes,” Advanced Synthesis & Catalysis, vol. 350, pp. 1013–1016, 2008.
[207]  R. Akiyama and S. Kobayashi, “Microencapsulated and related catalysts for organic chemistry and organic synthesis,” Chemical Reviews, vol. 109, no. 2, pp. 594–642, 2009.
[208]  C. A. Wang, Y. Zhang, J. Y. Shi, and W. Wang, “A self-supported polymeric MacMillan catalyst for homogeneous organocatalysis and heterogeneous recycling,” Chemistry—A European Journal, vol. 8, no. 6, pp. 1110–1114, 2013.
[209]  J. Seayad, A. M. Seayad, and B. List, “Catalytic asymmetric Pictet-Spengler reaction,” Journal of the American Chemical Society, vol. 128, no. 4, pp. 1086–1087, 2006.
[210]  S. Hoffmann, A. M. Seayad, and B. List, “A powerful Br？nsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines,” Angewandte Chemie International Edition, vol. 44, no. 45, pp. 7424–7427, 2005.
[211]  M. Rueping, E. Sugiono, C. Azap, T. Theissmann, and M. Bolte, “Enantioselective Br？nsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines,” Organic Letters, vol. 7, no. 17, pp. 3781–3783, 2005.
[212]  R. I. Storer, D. E. Carrera, Y. Ni, and D. W. C. MacMillan, “Enantioselective organocatalytic reductive amination,” Journal of the American Chemical Society, vol. 128, no. 1, pp. 84–86, 2006.
[213]  J. Zhou and B. List, “Organocatalytic asymmetric reaction cascade to substituted cyclohexylamines,” Journal of the American Chemical Society, vol. 129, no. 24, pp. 7498–7499, 2007.
[214]  G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, and J. C. Antilla, “Br？nsted acid-catalyzed imine amidation,” Journal of the American Chemical Society, vol. 127, no. 45, pp. 15696–15697, 2005.
[215]  T. Akiyama, Y. Tamura, J. Itoh, H. Morita, and K. Fuchibe, “Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Br？nsted acid: effect of the additive on the enantioselectivity,” Synlett, no. 1, Article ID Y07205ST, pp. 141–143, 2006.
[216]  Y. Su, M. J. Bouma, L. Alcaraz et al., “Organocatalytic enantioselective one-pot four-component ugi-type multicomponent reaction for the synthesis of epoxy-tetrahydropyrrolo[3,4-b]pyridin-5-ones,” Chemistry—A European Journal, vol. 18, no. 40, pp. 12624–12627, 2012.
[217]  D. J. Bayston, J. L. Fraser, M. R. Ashton, A. D. Baxter, M. E. C. Polywka, and E. Moses, “Preparation and use of a polymer supported BINAP hydrogenation catalyst,” The Journal of Organic Chemistry, vol. 63, p. 3137, 1998.
[218]  D. S. Kundu, J. Schmidt, C. Bleschke, A. Thomas, and S. Blechert, “A microporous binol-derived phosphoric acid,” Angewandte Chemie International Edition, vol. 51, no. 22, pp. 5456–5459, 2012.
[219]  Y. Huang, A. K. Unni, A. N. Thadani, and V. H. Rawal, “Single enantiomers from a chiral-alcohol catalyst,” Nature, vol. 424, no. 6945, p. 146, 2003.
[220]  H. M. Guo, L. Cheng, L. F. Cun, L. Z. Gong, A. Q. Mi, and Y. Z. Jiang, “L-Prolinamide-catalyzed direct nitroso aldol reactions of α-branched aldehydes: a distinct regioselectivity from that with L-proline,” Chemical Communications, no. 4, pp. 429–431, 2006.
[221]  N. T. McDougal and S. E. Schaus, “Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Br？nsted acids,” Journal of the American Chemical Society, vol. 125, no. 40, pp. 12094–12095, 2003.
[222]  P. Vachal and E. N. Jacobsen, “Structure-based analysis and optimization of a highly enantioselective catalyst for the strecker reaction,” Journal of the American Chemical Society, vol. 124, no. 34, pp. 10012–10014, 2002.
[223]  G. D. Joly and E. N. Jacobsen, “Thiourea-catalyzed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched α-amino phosphonic acids,” Journal of the American Chemical Society, vol. 126, p. 4102, 2004.
[224]  A. G. Wenzel and E. N. Jacobsen, “Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: enantioselective synthesis of β-aryl-β-amino acids,” Journal of the American Chemical Society, vol. 124, pp. 12964–12965, 2002.
[225]  D. E. Fuerst and E. N. Jacobsen, “Thiourea-catalyzed enantioselective cyanosilylation of ketones,” Journal of the American Chemical Society, vol. 127, no. 25, pp. 8964–8965, 2005.
[226]  M. S. Taylor and E. N. Jacobsen, “Highly enantioselective catalytic acyl-Pictet-Spengler reactions,” Journal of the American Chemical Society, vol. 126, no. 34, pp. 10558–10559, 2004.
[227]  M. S. Talyor, N. Tokunaga, and E. N. Jacobsen, “Enantioselective thiourea-catalyzed acyl-mannich reactions of isoquinolines,” Angewandte Chemie International Edition, vol. 44, pp. 6700–6704, 2005.
[228]  X. Li, C. Yang, J.-L. Jin, X.-S. Xue, and J.-P. Cheng, “Synthesis of optically enriched spirocyclic benzofuran-2-ones by bifunctional thiourea-base catalyzed double-Michael addition of benzofuran-2-ones to dienones,” Chemistry—An Asian Journal, vol. 8, no. 05, pp. 997–1003, 2013.
[229]  S.-R. Ban, X.-X. Zhu, Z.-P. Zhang, H.-Y. Xie, and Q.-S. Li, “Benzoylthiourea–pyrrolidine as another bifunctional organocatalyst: highly enantioselective michael addition of cyclohexanone to nitroolefins,” European Journal of Organic Chemistry, vol. 15, pp. 2977–2980, 2013.
[230]  M. Tsakos, C. G. Kokotos, and G. Kokotos, “Primary amine-thioureas with improved catalytic properties for “difficult” Michael reactions: efficient organocatalytic syntheses of (S)-baclofen, (R)-baclofen and (S)-phenibut,” Advanced Synthesis and Catalysis, vol. 354, no. 4, pp. 740–746, 2012.
[231]  M. J. O'Donnell, “The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters,” Accounts of Chemical Research, vol. 37, pp. 506–517, 2004.
[232]  B. Lygo and B. J. Andrews, “The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters,” Accounts of Chemical Research, vol. 37, pp. 518–525, 2004.
[233]  S.-K. Tian, R. Hong, and L. Deng, “Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base,” Journal of the American Chemical Society, vol. 125, no. 33, pp. 9900–9901, 2003.
[234]  T. B. Poulsen, C. Alemparte, and K. A. J？rgensen, “Enantioselective organocatalytic allylic amination,” Journal of the American Chemical Society, vol. 127, pp. 11614–11615, 2005.
[235]  M. Bella and K. A. J？rgensen, “Organocatalytic enantioselective conjugate addition to alkynones,” Journal of the American Chemical Society, vol. 126, pp. 5672–5673, 2004.
[236]  P. Melchiorre, “Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds,” Angewandte Chemie International Edition, vol. 51, no. 39, pp. 9748–9770, 2012.
[237]  E. Arceo and P. Melchiorre, “Extending the aminocatalytic HOMO-raising activation strategy: where is the limit?” Angewandte Chemie International Edition, vol. 51, no. 22, pp. 5290–5292, 2012.
[238]  C.-K. Pei and M. Shi, “Asymmetric cyclization reactions of allenoates with imines or α,β-unsaturated ketones catalyzed by organocatalysts derived from cinchona alkaloids,” Chemistry—A European Journal, vol. 18, no. 22, pp. 6712–6716, 2012.
[239]  A. Russo, G. Galdi, G. Croce, and A. Lattanzi, “Highly enantioselective epoxidation catalyzed by cinchona thioureas: synthesis of functionalized terminal epoxides bearing a quaternary stereogenic center,” Chemistry—A European Journal, vol. 18, no. 20, pp. 6152–6157, 2012.
[240]  A. Kumar and S. S. Chimni, “Organocatalytic asymmetric direct aldol reaction of pyruvic aldehyde dimethyl acetal with isatin derivatives,” European Journal of Organic Chemistry, vol. 2013, no. 22, pp. 4780–4876, 2013.
[241]  M.-X. Zhao, H. Zhou, W.-H. Tang, W.-S. Qu, and M. Shi, “Cinchona alkaloid-derived thiourea-catalyzed diastereo- and enantioselective [3+2]？cycloaddition reaction of isocyanoacetates to isatins: a facile access to optically active spirooxindole oxazolines,” Advanced Synthesis & Catalysis, vol. 355, no. 7, pp. 1277–1283, 2013.
[242]  F. Xu, M. Zacuto, N. Yoshikawa et al., “Asymmetric synthesis of telcagepant, a CGRP receptor antagonist for the treatment of migraine,” Journal of Organic Chemistry, vol. 75, no. 22, pp. 7829–7841, 2010.
[243]  G. Rassu, V. Zambrano, L. Pinna et al., “Direct regio-, diastereo-, and enantioselective vinylogous Michael addition of prochiral 3-alkylideneoxindoles to nitroolefins,” Advanced Synthesis & Catalysis, vol. 355, no. 9, pp. 1881–1886, 2013.
[244]  S. Brandau, A. Landa, J. Franzén, M. Marigo, and K. A. J？rgensen, “Organocatalytic conjugate addition of malonates to alpha,beta-unsaturated aldehydes: asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones,” Angewandte Chemie International Edition, vol. 45, no. 26, pp. 4305–4309, 2006.
[245]  L. J. Hounjet, C. Bannwarth, C. N. Garon, C. B. Caputo, S. Grimme, and D. W. Stephan, “Combinations of ethers and B(C6F5)3 function as hydrogenation catalysts,” Angewandte Chemie International Edition, vol. 52, no. 29, pp. 7492–7495, 2013.
[246]  X.-F. Cai, M.-W. Chen, Z.-S. Ye et al., “Asymmetric transfer hydrogenation of 3-nitroquinolines: facile access to cyclic nitro compounds with two contiguous stereocenters,” Chemistry—An Asian Journal, vol. 8, no. 7, pp. 1381–1385, 2013.
[247]  M. Kitamura, S. Shirakawa, and K. Maruoka, “Powerful chiral phase-transfer catalysts for the asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids,” Angewandte Chemie International Edition, vol. 44, pp. 1549–1551, 2005.
[248]  T. Ooi, Y. Arimura, Y. Hiraiwa et al., “Highly enantioselective monoalkylation of p-chlorobenzaldehyde imine of glycine tert-butyl ester under mild phase-transfer conditions,” Tetrahedron: Asymmetry, vol. 17, pp. 603–606, 2006.
[249]  T. Ooi and K. Maruoka, “Development and applications of C2-symmetric, chiral, phase-transfer catalysts,” Aldrichimica Acta, vol. 40, no. 3, pp. 77–86, 2007.
[250]  E. J. Corey, R. K. Bakshi, and S. Shibata, “Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications,” Journal of the American Chemical Society, vol. 109, pp. 5551–5553, 1987.
[251]  E. J. Corey, R. K. Bakshi, S. Shibata, C. P. Chen, and V. K. Singh, “A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses,” Journal of the American Chemical Society, vol. 109, pp. 7925–7926, 1987.
[252]  E. H. M. Kirton, G. Tughan, R. E. Morris, and R. A. Field, “Rationalising the effect of reducing agent on the oxazaborolidine-mediated asymmetric reduction of N-substituted imines,” Tetrahedron Letters, vol. 45, pp. 853–855, 2004.
[253]  B. T. Cho and Y. S. Chun, “Enantioselective synthesis of optically active metolachlor via asymmetric reduction,” Tetrahedron Asymmetry, vol. 3, no. 3, pp. 337–340, 1992.
[254]  B. T. Cho and Y. S. Chun, “Asymmetric reduction of N-substituted ketimines with the reagent prepared from borane and (S)-(–)-2-amino-3-methyl-1,1-diphenylbutan-1-ol (itsuno's reagent): enantioselective synthesis of optically active secondary amines,” Journal of the Chemical Society, Perkin Transactions, vol. 1, pp. 3200–3201, 1990.
[255]  R. D. Tillyer, C. Boudreau, D. Tschaen, U.-H. Dolling, and P. J. Reider, “Asymmetric reduction of keto oxime ethers using oxazaborolidine reagents. The enantioselective synthesis of cyclic amino alcohols,” Tetrahedron Letters, vol. 36, no. 25, pp. 4337–4340, 1995.
[256]  D. H. Ryu and E. J. Corey, “Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition,” Journal of the American Chemical Society, vol. 125, pp. 6388–6390, 2003.
[257]  Y. Tu, Z.-X. Wang, and Y. Shi, “An efficient asymmetric epoxidation method for trans-olefins mediated by a fructose-derived ketone,” Journal of the American Chemical Society, vol. 118, no. 40, pp. 9806–9807, 1996.
[258]  Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, and Y. Shi, “An efficient catalytic asymmetric epoxidation method,” Journal of the American Chemical Society, vol. 119, no. 46, pp. 11224–11235, 1997.
[259]  Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, and Y. Shi, “An efficient catalytic asymmetric epoxidation method,” Journal of the American Chemical Society, vol. 119, no. 46, pp. 11224–11235, 1997.
[260]  M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, and K. A. J？rgensen, “Asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes with hydrogen peroxide,” Journal of the American Chemical Society, vol. 127, no. 19, pp. 6964–6965, 2005.
[261]  N. Marion, S. Díez-González, and S. P. Nolan, “Inside cover: a molecular solomon link (Angew. Chem. Int. Ed. 1-2/2007),” Angewandte Chemie International Edition, vol. 46, p. 2, 2007.
[262]  M. S. Kerr and T. Rovis, “Enantioselective synthesis of quaternary stereocenters via a catalytic asymmetric stetter reaction,” Journal of the American Chemical Society, vol. 126, no. 29, pp. 8876–8877, 2004.
[263]  M. He, J. R. Struble, and J. W. Bode, “Highly enantioselective azadiene diels？alder reactions catalyzed by chiral N-heterocyclic carbenes,” Journal of the American Chemical Society, vol. 128, pp. 8418–8420, 2006.
[264]  M. He, G. J. Uc, and J. W. Bode, “Chiral N-heterocyclic carbene catalyzed, enantioselective oxodiene Diels-Alder reactions with low catalyst loadings,” Journal of the American Chemical Society, vol. 128, pp. 15088–15089, 2006.
[265]  P.-C. Chiang, J. Kaeobamrung, and J. W. Bode, “Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-Cope reactions,” Journal of the American Chemical Society, vol. 129, no. 12, pp. 3520–3521, 2007.
[266]  S. S. Sohn and J. W. Bode, “N-heterocyclic carbene catalyzed C–C bond cleavage in redox esterifications of chiral formylcyclopropanes,” Angewandte Chemie International Edition, vol. 45, pp. 6021–6024, 2006.
[267]  A. Grossmann and D. Enders, “N-heterocyclic carbene catalyzed domino reactions,” Angewandte Chemie International Edition, vol. 51, no. 2, pp. 314–325, 2012.
[268]  D. Enders, R. Hahn, and I. Atodiresei, “Asymmetric synthesis of functionalized tetrahydronaphthalenes via an organocatalytic nitroalkane-michael/henry domino reaction,” Advanced Synthesis & Catalysis, vol. 355, no. 6, pp. 1126–1136, 2013.
[269]  H. Pellissier, “Recent developments in asymmetric organocatalytic domino reactions,” Advanced Synthesis & Catalysis, vol. 354, no. 2-3, pp. 237–294, 2012.
[270]  L. Wu, Y. Wang, H. Song, L. Tang, Z. Zhou, and C. Tang, “Enantioselective organocatalytic domino Michael/aldol reactions: an efficient procedure for the stereocontrolled construction of 2H-thiopyrano[2,3-b]quinoline scaffolds,” Chemistry—An Asian Journal, vol. 8, pp. 2204–2210, 2013.
[271]  J. Zhao, C. Mück-Lichtenfeld, and A. Studer, “Cooperative N-heterocyclic carbene (NHC) and ruthenium redox catalysis: oxidative esterification of aldehydes with air as the terminal oxidant,” Advanced Synthesis & Catalysis, vol. 355, no. 6, pp. 1098–1106, 2013.
[272]  R. Blanc, P. Nava, M. Rajzman, L. Commeiras, and J.-L. Parrain, “N-Heterocyclic carbene mediated organocatalytic transfer of tin onto aldehydes: an easy access to syn-diols and mechanistic studies,” Advanced Synthesis & Catalysis, vol. 354, no. 10, pp. 2038–2048, 2012.
[273]  S. De Sarkar, A. Biswas, R. C. Samanta, and A. Studer, “Catalysis with N-heterocyclic carbenes under oxidative conditions,” Chemistry—A European Journal, vol. 19, no. 15, pp. 4664–4678, 2013.
[274]  H. U. Vora, P. Wheeler, and T. Rovis, “Exploiting acyl and enol azolium intermediates via N-hetero-cyclic carbene-catalyzed reactions of α-reducible aldehydes,” Advanced Synthesis & Catalysis, vol. 354, no. 9, pp. 1617–1639, 2012.
[275]  J. Mo, L. Shen, and Y. R. Chi, “Direct β-activation of saturated aldehydes to formal Michael acceptors through oxidative NHC catalysis,” Angewandte Chemie International Edition, vol. 52, no. 33, pp. 8588–8591, 2013.
[276]  M. Hans, J. Wouters, A. Demonceau, and L. Delaude, “Mechanistic insight into the staudinger reaction catalyzed by N-heterocyclic carbenes,” Chemistry—A European Journal, vol. 19, no. 29, pp. 9668–9676, 2013.
[277]  W. Raimondi, D. Bonne, and J. Rodriguez, “1,2-dicarbonyl compounds as pronucleophiles in organocatalytic asymmetric transformations,” Angewandte Chemie International Edition, vol. 51, no. 1, pp. 40–42, 2012.
[278]  A. Rai and L. D. S. Yadav, “Cyclopropenone-catalyzed direct conversion of aldoximes and primary amides into nitriles,” European Journal of Organic Chemistry, vol. 10, pp. 1889–1893, 2013.
[279]  J. Marco-Martínez, V. Marcos, S. Reboredo, S. Filippone, and N. Martín, “Asymmetric organocatalysis in fullerenes chemistry: enantioselective phosphine-catalyzed cycloaddition of allenoates onto C60,” Angewandte Chemie International Edition, vol. 52, no. 19, pp. 5115–5119, 2013.
[280]  A.-L. Lee, “Organocatalyzed carbonyl–olefin metathesis,” Angewandte Chemie International Edition, vol. 52, no. 17, pp. 4524–4525, 2013.
[281]  F. Kniep, S. H. Jungbauer, Q. Zhang et al., “Organocatalysis by neutral multidentate halogen-bond donors,” Angewandte Chemie International Edition, vol. 52, no. 27, pp. 7028–7032, 2013.
[282]  J. H. Kim, I. Coric, S. Vellalath, and B. List, “The catalytic asymmetric acetalization,” Angewandte Chemie International Edition, vol. 52, no. 16, pp. 4474–4477, 2013.
[283]  P. Chauhan and S. S. Chimni, “Organocatalytic enantioselective Morita-Baylis-Hillman reaction of maleimides with isatins,” Asian Journal of Organic Chemistry, vol. 2, no. 7, pp. 586–592, 2013.
[284]  P. Chauhan, J. Kaur, and S. S. Chimni, “Asymmetric organocatalytic addition reactions of maleimides: a promising approach towards the synthesis of chiral succinimide derivatives,” Chemistry—An Asian Journal, vol. 8, no. 2, pp. 328–346, 2013.
[285]  C. C. J. Loh and D. Enders, “Exploiting the electrophilic properties of indole intermediates: new options in designing asymmetric reactions,” Angewandte Chemie International Edition, vol. 51, no. 1, pp. 46–48, 2012.
[286]  A. Martínez, M. J. Webber, S. Müller, and B. List, “Versatile access to chiral indolines by catalytic asymmetric fischer indolization,” Angewandte Chemie International Edition, vol. 52, no. 36, pp. 948–9490, 2013.
[287]  Z. Shi and T.-P. Loh, “Organocatalytic synthesis of highly functionalized pyridines at room temperature,” Angewandte Chemie International Edition, vol. 52, no. 33, pp. 8584–8587, 2013.
[288]  A. V. Malkov, S. Stoncius, M. Bell et al., “Mechanistic dichotomy in the asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by chiral pyridine N-oxides,” Chemistry—A European Journal, vol. 19, no. 28, pp. 9167–9185, 2013.
[289]  K. Shibatomi and A. Narayama, “Catalytic enantioselective α-chlorination of carbonyl compounds,” Asian Journal of Organic Chemistry, vol. 2, no. 10, pp. 812–823, 2013.
[290]  C. C. J. Loh and D. Enders, “Merging organocatalysis and gold catalysis—a critical evaluation of the underlying concepts,” Chemistry—A European Journal, vol. 18, no. 33, pp. 10212–10225, 2012.
[291]  H.-N. Yuan, S. Wang, J. Nie, W. Meng, Q. Yao, and J.-A. Ma, “Hydrogen-bond-directed enantioselective decarboxylative Mannich reaction of β-ketoacids with ketimines: application to the synthesis of anti-HIV drug DPC 083,” Angewandte Chemie International Edition, vol. 52, no. 14, pp. 3869–3873, 2013.
[292]  Y. Hayashi, D. Sakamoto, H. Shomura, and D. Hashizume, “Asymmetric Mannich reaction of α-keto imines catalyzed by diarylprolinol silyl ether,” Chemistry—A European Journal, vol. 19, no. 24, pp. 7678–7681, 2013.
[293]  W.-Q. Zhang, L.-F. Cheng, J. Yu, and L.-Z. Gong, “A chiral bis(betaine) catalyst for the mannich reaction of azlactones and aliphatic imines,” Angewandte Chemie International Edition, vol. 51, no. 17, pp. 4085–4088, 2012.
[294]  L. Hong and R. Wang, “Recent advances in asymmetric organocatalytic construction of 3,3′-spirocyclic oxindoles,” Advanced Synthesis & Catalysis, vol. 355, no. 6, pp. 1023–1052, 2013.
[295]  M.-X. Wei, C.-T. Wang, J.-Y. Du et al., “Enantioselective synthesis of Amaryllidaceae alkaloids (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine,” Chemistry—An Asian Journal, vol. 8, no. 9, pp. 1966–1971, 2013.
[296]  H.-J. Yang, F.-J. Xiong, X.-F. Chen, and F.-E. Chen, “Highly enantioselective thiolysis of prochiral cyclic anhydrides catalyzed by amino alcohol bifunctional organocatalysts and its application to the synthesis of pregabalin,” European Journal of Organic Chemistry, vol. 2013, no. 21, pp. 4495–4489, 2013.
[297]  R. Selke and M. Capka, “Carbohydrate phosphinites as chiral ligands for asymmetric syntheses catalyzed by complexes: part VIII: immobilization of cationic rhodium(I) chelates of phenyl 4,6-O-(R)-benzylidene-2,3-bis(O-diphenylphosphino)-β-D-glucopyranoside on silica,” Journal of Molecular Catalysis, vol. 63, pp. 319–334, 1990.
[298]  M. Ichikawa, “‘Ship-in-Bottle’ catalyst technology. Novel templating fabrication of platinum group metals nanoparticles and wires in micro/mesopores,” Platinum Metals Review, vol. 44, no. 1, pp. 3–14, 2000.
[299]  V. Trevisan, M. Signoretto, S. Colonna, V. Pironti, and G. Strukul, “Microencapsulated chloroperoxidase as a recyclable catalyst for the enantioselective oxidation of sulfides with hydrogen peroxide,” Angewandte Chemie International Edition, vol. 43, no. 31, pp. 4097–4099, 2004.
[300]  á. Zsigmond, F. Notheisz, G. Csjernyik, and J.-E. B？ckvall, “Ruthenium-catalyzed aerobic oxidation of alcohols on zeolite-encapsulated cobalt salophen catalyst,” Topics in Catalysis, vol. 19, no. 1, pp. 119–124, 2002.
[301]  N. Legagneux, E. Jeanneau, A. Thomas et al., “Grafting reaction of platinum organometallic complexes on silica-supported or unsupported heteropolyacids,” Organometallics, vol. 30, no. 7, pp. 1783–1793, 2011.
[302]  Y. Wan, F. Zhang, Y. Lu, and H. Li, “Immobilization of Ru(II) complex on functionalized SBA-15 and its catalytic performance in aqueous homoallylic alcohol isomerization,” Journal of Molecular Catalysis A, vol. 267, pp. 165–172, 2007.
[303]  D. R. Burri, I. R. Shaikh, K.-M. Choi, and S.-E. Park, “Facile heterogenization of homogeneous ferrocene catalyst on SBA-15 and its hydroxylation activity,” Catalysis Communications, vol. 8, no. 4, pp. 731–735, 2007.
[304]  M. Kuroki, T. Asefa, W. Whitnal et al., “Synthesis and properties of 1,3,5-benzene periodic mesoporous organosilica (PMO): novel aromatic PMO with three point attachments and unique thermal transformations,” Journal of the American Chemical Society, vol. 124, no. 46, pp. 13886–13895, 2002.
[305]  T. Maschmeyer, F. Rey, G. Sankar, and J. M. Thomas, “Heterogeneous catalysts obtained by grafting metallocene complexes onto mesoporous silica,” Nature, vol. 378, pp. 159–162, 1995.
[306]  L. Hamidipour, Z. Ghasemzadeh, F. Farzaneh, and M. Ghandi, “Immobilization of Cu(II)-histidine complex on Al-MCM-41 as catalyst for epoxidation of alkenes,” Journal of Sciences, vol. 23, no. 1, pp. 29–36, 2012.
[307]  J. G. Mesu, D. Baute, H. J. Tromp, E. E. Van Faassen, and B. M. Weckhuysen, “Synthesis and characterization of zeolite encaged enzyme-mimetic copper histidine complexes,” Studies in Surface Science and Catalysis, vol. 143, pp. 287–293, 2002.
[308]  B. M. Weckhuysen, A. A. Verberckmoes, L. Fu, and R. A. Schoonheydt, “Zeolite-encapsulated copper(II) amino acid complexes: synthesis, spectroscopy, and catalysis,” Journal of Physical Chemistry, vol. 100, no. 22, pp. 9456–9461, 1996.
[309]  D. Xuereb, J. Dzierzak, and R. Raja, “Biomimetic single-site heterogeneous catalysts: design strategies and catalytic potential,” in Heterogenized Homogeneous Catalysts For Fine Chemicals Production, vol. 33 of Catalysis by Metal Complexes, pp. 37–63, 2010.
[310]  P. Barbaro and F. Liguori, Eds., Heterogenized Homogeneous Catalysts for Fine Chemicals Production, vol. 33 of Materials and Processes Series: Catalysis by Metal Complexes, Springer, 2010.
[311]  Z. An, W. Zhang, H. Shi, and J. He, “An effective heterogeneous l-proline catalyst for the asymmetric aldol reaction using anionic clays as intercalated support,” Journal of Catalysis, vol. 241, pp. 319–327, 2006.
[312]  J. W. Wiench, Y. S. Avadhut, N. Maity et al., “Characterization of covalent linkages in organically functionalized MCM-41 mesoporous materials by solid-state NMR and theoretical calculations,” Journal of Physical Chemistry B, vol. 111, no. 15, pp. 3877–3885, 2007.
[313]  Q. Gao, W. Xu, Y. Xu et al., “Amino acid adsorption on mesoporous materials: influence of types of amino acids, modification of mesoporous materials, and solution conditions,” The Journal of Physical Chemistry B, vol. 112, no. 7, pp. 2261–2267, 2008.
[314]  S. Luo, J. Li, L. Zhang, H. Xu, and J. P. Cheng, “Noncovalently supported heterogeneous chiral amine catalysts for asymmetric direct aldol and Michael addition reactions,” Chemistry—A European Journal, vol. 14, no. 4, pp. 1273–1281, 2008.
[315]  C. Aprile, F. Giacalone, M. Gruttadauria et al., “New ionic liquid-modified silica gels as recyclable materials for l-proline- or H-Pro-Pro-Asp-NH2-catalyzed aldol reaction,” Green Chemistry, vol. 9, no. 12, pp. 1328–1334, 2007.
[316]  I. Hermans, J. Van Deun, K. Houthoofd, J. Peeters, and P. A. Jacobs, “Silica-immobilized N-hydroxyphthalimide: an efficient heterogeneous autoxidation catalyst,” Journal of Catalysis, vol. 251, no. 1, pp. 204–212, 2007.
[317]  K. Yamaguchi, T. Imago, Y. Ogasawara, J. Kasai, M. Kotani, and N. Mizuno, “An immobilized organocatalyst for cyanosilylation and epoxidation,” Advanced Synthesis and Catalysis, vol. 348, no. 12-13, pp. 1516–1520, 2006.
[318]  H. Hagiwara, S. Inotsume, M. Fukushima, T. Hoshi, and T. Suzuki, “Heterogeneous amine catalyst grafted on amorphous silica: an effective organocatalyst for microwave-promoted Michael reaction of 1,3-dicarbonyl compounds in water,” Chemistry Letters, vol. 35, no. 8, pp. 926–927, 2006.
[319]  A. Corma and H. Garcia, “Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis,” Advanced Synthesis Catalysis, vol. 348, pp. 1391–1412, 2006.
[320]  C. Ayats, A. H. Henseler, and M. A. Pericás, “A solid-supported organocatalyst for continuous-flow enantioselective aldol reactions,” ChemSusChem, vol. 5, no. 2, pp. 320–325, 2012.
[321]  D. Font, C. Jimeno, and M. A. Pericàs, “Polystyrene-supported hydroxyproline: an insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water,” Organic Letters, vol. 8, pp. 4653–4655, 2006.
[322]  D. Font, S. Sayalero, C. Jimeno, and M. A. Pericàs, “Toward an artificial aldolase,” Organic Letters, vol. 10, pp. 337–340, 2008.
[323]  D. Font, S. Sayalero, A. Bastero, C. Jimeno, and M. A. Pericàs, “Toward an artificial aldolase,” Organic Letters, vol. 12, p. 2678, 2010.
[324]  M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, and G. Celentano, “Poly(ethylene-glycol)-supported proline: a recyclable aminocatalyst for the enantioselective synthesis of γ-nitroketones by conjugate addition,” Journal of Molecular Catalysis A, vol. 204-205, pp. 157–163, 2003.
[325]  D. Q. Xu, S. P. Luo, Y. F. Wang et al., “Organocatalysts wrapped around by poly(ethylene glycol)s (PEGs): a unique host-guest system for asymmetric Michael addition reactions,” Chemical Communications, no. 42, pp. 4393–4395, 2007.
[326]  A. M. Caminade, A. Ouali, M. Keller, and J. P. Majoral, “Organocatalysis with dendrimers,” Chemical Society Reviews, vol. 41, pp. 4113–4125, 2012.
[327]  L. Zhang, S. Luo, and J.-P. Cheng, “Non-covalent immobilization of asymmetric organocatalysts,” Catalysis Science and Technology, vol. 1, no. 4, pp. 507–516, 2011.
[328]  B.-C. Hong, H.-C. Tseng, and S.-H. Chen, “Synthesis of aromatic aldehydes by organocatalytic [4+2] and [3+3] cycloaddition of α,β-unsaturated aldehydes,” Tetrahedron, vol. 63, no. 13, pp. 2840–2850, 2007.
[329]  M. J. Gaunt, C. C. C. Johansson, A. McNally, and N. T. Vo, “Enantioselective organocatalysis,” Drug Discovery Today, vol. 12, no. 1-2, pp. 8–27, 2007.
[330]  D. J. Xuereb and R. Raja, “Design strategies for engineering selectivity in bio-inspired heterogeneous catalysts,” Catalysis Science and Technology, vol. 1, no. 4, pp. 517–534, 2011.
[331]  D. J. Xuereb, Strategies for organocatalyst heterogenisation and performance in selective transformations [Ph.D. thesis], University of Southampton, 2012.
[332]  D. E. De Vos, I. F. J. Vankelecom, and P. A. Jacobs, Eds., Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, Germany, 2000.
[333]  J. Zhou, J. Wan, X. Ma, and W. Wang, “Copolymer-supported heterogeneous organocatalyst for asymmetric aldol addition in aqueous medium,” Organic & Biomolecular Chemistry, vol. 10, pp. 4179–4185, 2012.
[334]  P. C. Bulman Page, A. Mace, D. Arquier et al., “Towards heterogeneous organocatalysis: chiral iminium cations supported on porous materials for enantioselective alkene epoxidation,” Catalysis Science & Technology, vol. 3, pp. 2330–2339, 2013.
[335]  J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjaersgaard, and K. A. J？rgensen, “A general organocatalyst for direct α-functionalization of aldehydes: stereoselective C–C, C–N, C–F, C–Br, and C–S bond-forming reactions. Scope and mechanistic insights,” Journal of the American Chemical Society, vol. 127, no. 51, pp. 18296–18304, 2005.
[336]  M. Fochi, L. Gramigna, A. Mazzanti et al., “Solvent-free non-covalent organocatalysis: enantioselective addition of nitroalkanes to alkylideneindolenines as a flexible gateway to optically active tryptamine derivatives,” Advanced Synthesis & Catalysis, vol. 354, pp. 71373–71380, 2012.
[337]  Y. Zhang, Y. Zhang, Y. L. Sun et al., “4-(N,N-dimethylamino)pyridine-embedded nanoporous conjugated polymer as a highly active heterogeneous organocatalyst,” Chemistry—A European Journal, vol. 18, no. 20, pp. 6328–6334, 2012.
[338]  C. A. Wang, Y. Zhang, J. Y. Shi, and W. Wang, “A self-supported polymeric MacMillan catalyst for homogeneous organocatalysis and heterogeneous recycling,” Chemistry—An Asian Journal, vol. 8, no. 6, pp. 1110–1114, 2013.
[339]  V. Lucchini, M. Noè, M. Selva, M. Fabris, and A. Perosa, “Cooperative nucleophilic-electrophilic organocatalysis by ionic liquids,” Chemical Communications, vol. 48, no. 42, pp. 5178–5180, 2012.
[340]  D. Kühbeck, G. Saidulu, K. R. Reddy, and D. D. Díaz, “Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation,” Green Chemistry, vol. 14, pp. 378–392, 2012.
[341]  S. Verma, S. L. Jain, and B. Sain, “An efficient biomaterial supported bifunctional organocatalyst (ES–S C5H5NH+) for the synthesis of β-amino carbonyls,” Organic & Biomolecular Chemistry, vol. 9, pp. 2314–2318, 2011.
[342]  M. S. DeClue and J. S. Siegel, “Polysiloxane-bound ligand accelerated catalysis: a modular approach to heterogeneous and homogeneous macromolecular asymmetric dihydroxylation ligands,” Organic & Biomolecular Chemistry, vol. 2, pp. 2287–2298, 2004.
[343]  G. Kardos and T. Soós, “Tether-free immobilized bifunctional squaramide organocatalysts for batch and flow reactions,” European Journal of Organic Chemistry, vol. 2013, no. 21, pp. 4490–4494, 2013.
[344]  P. Kasaplar, P. Riente, C. Hartmann, and M. A. Pericàs, “A polystyrene-supported, highly recyclable squaramide organocatalyst for the enantioselective Michael addition of 1,3-dicarbonyl compounds to β-nitrostyrenes,” Advanced Synthesis & Catalysis, vol. 354, no. 16, pp. 2905–2910, 2013.
[345]  K. E. Alza, C. Rodríguez-Escrich, S. Sayalero, A. Bastero, and M. A. Pericàs, “A solid-supported organocatalyst for highly stereoselective, batch, and continuous-flow mannich reactions,” Chemistry—A European Journal, vol. 15, no. 39, pp. 10167–10172, 2009.
[346]  P. Riente, J. Yadav, and M. A. Pericàs, “A solid-supported organocatalyst for continuous-flow enantioselective aldol reactions,” ChemSusChem, vol. 5, no. 2, pp. 320–325, 2012.
[347]  M. Kotke and P. Schreiner, “(Thio)Urea Organocatalysts,” in Hydrogen Bonding in Organic Synthesis, P. M. Pihko, Ed., pp. 141–352, Wiley-VCH, 2009.
[348]  Y. Takemoto, “Development of chiral thiourea catalysts and its application to asymmetric catalytic reactions,” Chemical and Pharmaceutical Bulletin, vol. 58, pp. 593–601, 2010.
[349]  M. Tsakos, C. G. Kokotos, and G. Kokotos, “Primary amine-thioureas with improved catalytic properties for “difficult” Michael reactions: efficient organocatalytic syntheses of (S)-baclofen, (R)-baclofen and (S)-phenibut,” Advanced Synthesis and Catalysis, vol. 354, no. 4, pp. 740–746, 2012.
[350]  M. Tsakos and C. G. Kokotos, “Organocatalytic “Difficult” Michael reaction of ketones with nitrodienes utilizing a primary amine—thiourea based on di-tert-butyl aspartate,” European Journal of Organic Chemistry, vol. 2012, no. 3, pp. 576–580, 2012.
[351]  J. Hine, S.-M. Linden, and V. M. Kanagasabapathy, “1,8-Biphenylenediol is a double-hydrogen-bonding catalyst for reaction of an epoxide with a nucleophile,” Journal of the American Chemical Society, vol. 107, no. 4, pp. 1082–1083, 1985.
[352]  J. Hine, S. M. Linden, and V. M. Kanagasabapathy, “Double-hydrogen-bonding catalysis of the reaction of phenyl glycidyl ether with diethylamine by 1,8-biphenylenediol,” The Journal of Organic Chemistry, vol. 50, pp. 5096–5099, 1985.
[353]  C. K. De, E. G. Klauber, and D. Seidel, “Merging nucleophilic and hydrogen bonding catalysis: an anion binding approach to the kinetic resolution of amines,” Journal of the American Chemical Society, vol. 131, pp. 17060–17061, 2009.
[354]  R. P. Herrera, V. Sgarzani, L. Bernardi, and A. Ricci, “Catalytic enantioselective friedel-crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst,” Angewandte Chemie International Edition, vol. 44, pp. 6576–6579, 2005.
[355]  “Special issue on “Organocatalysis”,” Advanced Synthesis & Catalysis, vol. 346, no. 9-10, 2004.
[356]  F. Cozzi, “Immobilization of organic catalysts: when, why, and how,” Advanced Synthesis & Catalysis, vol. 348, pp. 1367–1390, 2006.
[357]  T. E. Kristensen and T. Hansen, “Polymer-supported chiral organocatalysts: synthetic strategies for the road towards affordable polymeric immobilization,” European Journal of Organic Chemistry, no. 17, pp. 3179–3204, 2010.
[358]  M. Benaglia, F. Cozzi, and A. Puglisi, “Polymer-supported organic catalysts,” Chemical Reviews, vol. 103, no. 9, pp. 3401–3429, 2003.
[359]  M. Benaglia, Ed., Recoverable and Recyclable Catalysts, John Wiley & Sons, Chichester, UK, 2009.
[360]  J. Lu and P. H. Toy, “Organic polymer supports for synthesis and for reagent and catalyst immobilization,” Chemical Reviews, vol. 109, no. 2, pp. 815–838, 2009.
[361]  M. Gruttadauria, F. Giacalone, and R. Noto, “Supported proline and proline-derivatives as recyclable organocatalysts,” Chemical Society Reviews, vol. 37, no. 8, pp. 1666–1688, 2008.
[362]  F. Calderón, R. Fernández, F. Sánchez, and A. Fernández-Mayoralas, “Asymmetric aldol reaction using immobilized proline on mesoporous support,” Advanced Synthesis & Catalysis, vol. 347, no. 10, pp. 1395–1403, 2005.
[363]  L. Qin, L. Zhang, Q. Jin, J. Zhang, B. Han, and M. Liu, “Supramolecular assemblies of amphiphilic L-proline regulated by compressed CO2 as a recyclable organocatalyst for the asymmetric aldol reaction,” Angewandte Chemie International Edition, vol. 52, no. 30, pp. 7761–7765.
[364]  S. Luo, J. Li, L. Zhang, H. Xu, and J.-P. Cheng, “Noncovalently supported heterogeneous chiral amine catalysts for asymmetric direct aldol and Michael addition reactions,” Chemistry—A European Journal, vol. 14, no. 4, pp. 1273–1281, 2008.
[365]  H. Hagiwara, S. Inotsume, M. Fukushima, T. Hoshi, and T. Suzuki, “Heterogeneous amine catalyst grafted on amorphous silica: an effective organocatalyst for microwave-promoted Michael reaction of 1,3-dicarbonyl compounds in water,” Chemistry Letters, vol. 35, no. 8, pp. 926–927, 2006.
[366]  I. Hermans, J. Van Deun, K. Houthoofd, J. Peeters, and P. A. Jacobs, “Silica-immobilized N-hydroxyphthalimide: an efficient heterogeneous autoxidation catalyst,” Journal of Catalysis, vol. 251, no. 1, pp. 204–212, 2007.
[367]  A. Corma and H. Garcia, “Silica-bound homogenous catalysts as recoverable and reusable catalysts in organic synthesis,” Advanced Synthesis & Catalysis, vol. 348, pp. 1391–1412, 2006.
[368]  K. Yamaguchi, T. Imago, Y. Ogasawara, J. Kasai, M. Kotani, and N. Mizuno, “An immobilized organocatalyst for cyanosilylation and epoxidation,” Advanced Synthesis and Catalysis, vol. 348, no. 12-13, pp. 1516–1520, 2006.
[369]  A. Córdova and J. Hafrén, “Direct Homogeneous and Heterogeneous Organic Acid and Amino Acid-Catalyzed Modification of Amines and Alcohols,” International Patent WO 2006068611 A1 20060629.
[370]  R. S. Verma and V. Polshettiwar, “Magnetic nanoparticle-supported glutathione as a sustainable organocatalyst,” Patent no.: US, 8324125 B2, December 2012.
[371]  R. C. Garrett and H. Yang, “Sulfonamide-Based Organocatalysis and Method for their Use,” Patent no.: US 8, 399, 684 B2, March 2013.
[372]  A. M. Caminade, C. O. Turrin, R. Laurent, A. Ouali, and B. Delavaux-Nicot, Eds., Dendrimers Towards Catalytic Material and Biomedical Uses, John Wiley & Sons, Chichester, UK, 2011.
[373]  P. Servin, R. Laurent, L. Gonsalvi et al., “Grafting of water-soluble phosphines to dendrimers and their use in catalysis: positive dendritic effects in aqueous media,” Dalton Transactions, no. 23, pp. 4432–4434, 2009.
[374]  M. Keller, A. Perrier, R. Linhardt, et al., “Dendrimers or nanoparticles as supports for the design of efficient and recoverable organocatalysts?” Advanced Synthesis & Catalysis, vol. 355, no. 9, pp. 1748–1754, 2013.
[375]  Thematic Series “Organocatalysis” (Guest Editor: Benjamin List) Beilstein Journal of Organic Chemistry, 2012, http://www.beilstein-journals.org/bjoc/browse/singleSeries.htm?sn=27.
[376]  Y. S. Lee, M. M. Alam, and R. S. Keri, “Enantioselective reactions of N-acyliminium ions using chiral organocatalysts,” Chemistry—An Asian Journal, vol. 8, no. 12, pp. 2906–2919, 2013.
[377]  F. Lv, S. Liu, and W. Hu, “Recent advances in the use of chiral br？nsted acids as cooperative catalysts in cascade and multicomponent reactions,” Asian Journal of Organic Chemistry, vol. 2, no. 10, pp. 824–836, 2013.
[378]  W. Yan, X. Shi, and C. Zhong, “Secondary amines as lewis bases in nitroalkene activation,” Asian Journal of Organic Chemistry, vol. 2, no. 11, pp. 904–914, 2013.
[379]  S. Ulf and M. Rainer, “Recent advances in organocatalytic methods for asymmetric C–C bond formation,” Chemistry—A European Journal, vol. 19, no. 43, pp. 14346–14396, 2013.
[380]  S. Narayanaperumal, D. G. Rivera, R. C. Silva, and M. W. Paix？o, “Terpene-derived bifunctional thioureas in asymmetric organocatalysis,” ChemCatChem, vol. 5, no. 10, pp. 2756–2773, 2013.
[381]  L.-W. Xu, “Powerful amino acid derived bifunctional phosphine catalysts bearing a hydrogen bond donor in asymmetric synthesis,” ChemCatChem, vol. 5, no. 10, pp. 2775–2784, 2013.
[382]  N. Kielland, C. J. Whiteoak, and A. W. Kleij, “Stereoselective synthesis with carbon dioxide,” Advanced Synthesis & Catalysis, vol. 355, no. 11-12, pp. 2115–2138, 2013.
[383]  S. Mohammadi, R. Heiran, R. P. Herrera, and E. Marqués-López, “Isatin as a strategic motif for asymmetric catalysis,” ChemCatChem, vol. 5, no. 8, pp. 2131–2148, 2013.

Full-Text

comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133

WeChat 1538708413