全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
Catalysts  2013 

An Ionic Liquid Solution of Chitosan as Organocatalyst

DOI: 10.3390/catal3040914

Keywords: ionic liquids, chitosan, Aldol reaction

Full-Text   Cite this paper   Add to My Lib

Abstract:

Chitosan, which is derived from the biopolymer chitin, can be readily dissolved in different ionic liquids. The resulting homogeneous solutions were applied in an asymmetric Aldol reaction. Depending on the type of ionic liquid used, high asymmetric inductions were found. The influence of different additives was also studied. The best results were obtained in [BMIM][Br] without an additive.

References

[1]  Berkessel, A.; Gr?ger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, Germany, 2005.
[2]  Dalko, P.I. Enantioselective Organocatalysis; Wiley-VCH: Weinheim, Germany, 2007.
[3]  Sereda, O.; Tabassum, S.; Wilhelm, R. Lewis acid organocatalysts. Top. Curr. Chem. 2010, 291, 349–394, doi:10.1007/128_2008_17.
[4]  Northrup, A.B.; MacMillan, D.W.C. The first general enantioselective catalytic Diels-Alder reaction with simple α,β-unsaturated ketones. J. Am. Chem. Soc. 2002, 124, 2458–2460, doi:10.1021/ja017641u.
[5]  Hajos, Z.G.; Parrish, D.R. Asymmetric synthesis of bicyclic intermediates of natural product chemistry. J. Org. Chem. 1974, 39, 1615–1621, doi:10.1021/jo00925a003.
[6]  Eder, U.; Sauer, G.; Wiechert, R. New type of asymmetric cyclization to optically active steroid CD partial structures. Angew. Chem. Int. Ed. Engl. 1971, 10, 496–497, doi:10.1002/anie.197104961.
[7]  List, B.; Lerner, R.A.; Barbas, C.F. Proline-catalyzed direct asymmetric Aldol reactions. J. Am. Chem. Soc. 2000, 122, 2395–2396, doi:10.1021/ja994280y.
[8]  Gr?ger, H.; Wilken, J. The application of l-proline as an enzyme mimic and further new asymmetric syntheses using small organic molecules as chiral catalysis. Angew. Chem. Int. Ed. 2001, 40, 529–532, doi:10.1002/1521-3773(20010202)40:3<529::AID-ANIE529>3.0.CO;2-X.
[9]  Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C.F. Amino acid Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond-Forming reactions. J. Am. Chem. Soc. 2001, 123, 5260–5267, doi:10.1021/ja010037z.
[10]  Xu, L.-W.; Lu, Y. Primary amino acids: Privileged catalysts in enantioselective organocatalysis. Org. Biomol. Chem. 2008, 6, 2047–2053, doi:10.1039/b803116a.
[11]  Gioa, C.; Ricci, A.; Bernardi, L.; Bourahla, K.; Tanchoux, N.; Robitzer, M.; Quignard, F. chitosan aerogel Beads as a Heterogeneous Organocatalyst for the asymmetric Aldol Reaction in the presence of water: An assessment of the effect of additives. Eur. J. Org. Chem. 2013, 588–594.
[12]  Ricci, A.; Bernardi, L.; Gioia, C.; Vierucci, S.; Robitzer, M.; Quignard, F. Chitosan aerogel: A recyclable, heterogeneous organocatalyst for the asymmetric direct aldol reaction in water. Chem. Commun. 2010, 6288–6290.
[13]  Reddy, K.R.; Rajgopal, K.; Maheswari, C.U.; Kantam, M.L. Chitosan hydrogel: A green and recyclable biopolymer catalyst for aldol and Knoevenagel reactions. New J. Chem. 2006, 30, 1549–1552, doi:10.1039/b610355c.
[14]  Kühbeck, D.; Saidulu, G.; Reddy, K.R.; Diaz, D.D. Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation. Green Chem. 2012, 14, 378–392, doi:10.1039/c1gc15925a.
[15]  Dekamin, M.G.; Azimoshan, M.; Ramezani, L. Chitosan: A highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions. Green Chem. 2013, 15, 811–820, doi:10.1039/c3gc36901c.
[16]  Chtchigrovsky, M.; Primo, A.; Gonzalez, P.; Molvinger, K.; Robitzer, M.; Quignard, F.; Taran, F. Functionalized chitosan as a green, recyclable, biopolymer-supported catalyst for the [3 + 2] huisgen cycloaddition. Angew. Chem. Int. Ed. 2009, 48, 5916–5920, doi:10.1002/anie.200901309.
[17]  Pinkert, A.; Marsh, K.N.; Pang, S.S.; Staiger, M.P. Ionic liquids and Their Interaction with cellulose. Chem. Rev. 2009, 109, 6712–6728, doi:10.1021/cr9001947.
[18]  Barber, P.S.; Griggs, C.S.; Bonner, J.R.; Rogers, R.D. Electrospinning of chitin nanofibers directly from an ionic liquid extract of shrimp shells. Green Chem. 2013, 15, 601–607, doi:10.1039/c2gc36582k.
[19]  Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis, 2nd ed. ed.; Wiley-VCH: Weinheim, Germay, 2008; Volume 1–2.
[20]  Khan, S.S.; Shah, J.; Liebscher, J. Ionic-liquid tagged prolines as recycable organocatalysts for enantioselective α-aminoxylations of carbonyl compounds. Tetrahedron 2011, 67, 1812–1820, doi:10.1016/j.tet.2011.01.031.
[21]  Winkel, A.; Reddy, P.V.G.; Wilhelm, R. Recent advances in the synthesis and application of chiral ionic liquids. Synthesis 2008, 999–1016.
[22]  Jur?ík, V.; Wilhelm, R. The preparation of new enantiopure imidazolinium salts and their evaluation as catalysts and shift reagents. Tetrahedron 2006, 17, 801–810, doi:10.1016/j.tetasy.2006.02.021.
[23]  Winkel, A.; Wilhelm, R. New chiral ionic liquids Based on Imidazolinium salts. Tetrahedron 2009, 20, 2344–2350, doi:10.1016/j.tetasy.2009.09.015.
[24]  Winkel, A.; Wilhelm, R. New chiral ionic liquids based on enantiopure sulphate and sulfonate anions for chiral recognition. Eur. J. Org. Chem. 2010, 5817–5824, doi:10.1002/ejoc.201000801.
[25]  Hollóczki, O.; Gerhard, D.; Massone, K.; Szarvas, L.; Németh, B.; Veszprémi, T.; Nyulászi, L. Carbenes in ionic liquids. New. J. Chem. 2010, 34, 3004–3009, doi:10.1039/c0nj00380h.
[26]  Hollóczki, O.; Nyulászi, L. Neutral species from “non-protic” N-heterocyclic ionic liquids. Org. Biomol. Chem. 2011, 9, 2634–2640, doi:10.1039/c1ob00007a.
[27]  Kelemen, Z.; Hollóczki, O.; Nagy, J.; Nyulászi, L. An organocatalytic ionic liquid. Org. Biomol. Chem. 2011, 9, 5362–5364, doi:10.1039/c1ob05639e.
[28]  Xie, B.-H.; Li, W.; Liu, Y.; Li, H.-H.; Guan, Z.; He, Y.-H. The enzymeticasymmetric aldol reaction using acidic protease from Aspergillus usamii. Tetrahedron 2012, 68, 3160–3164, doi:10.1016/j.tet.2012.02.056.
[29]  Gauchot, V.; Schmitzer, A.R. Asymmetric Aldol Reaction catalyszed by the anion of an ionic liquid. J. Org. Chem. 2012, 77, 4917–4923, doi:10.1021/jo300737u.

Full-Text

comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133

WeChat 1538708413