%0 Journal Article
%T Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions
%A Matthias Leven
%A J£¿rg M. Neud£¿rfl
%A Bernd Goldfuss
%J Beilstein Journal of Organic Chemistry
%D 2013
%I 
%R 10.3762/bjoc.9.18
%X Four catalysts based on new amides of chiral 1,2-diamines and 2-sulfobenzoic acid have been developed. The alkali-metal salts of these betaine-like amides are able to form imines with enones, which are activated by Lewis acid interaction for nucleophilic attack by 4-hydroxycoumarin. The addition of 4-hydroxycoumarin to enones gives ee¡¯s up to 83% and almost quantitative yields in many cases. This novel type of catalysis provides an effective alternative to conventional primary amino catalysis were strong acid additives are essential components.
%K alkali metals
%K aminocatalysis
%K DFT-calculations
%K Lewis acids
%K Michael addition
%U http://dx.doi.org/10.3762/bjoc.9.18