Highly enantioselective Michael addition of acetone to nitroolefins catalyzed by chiral bifunctional primary amine-thiourea catalysts with acetic acid

Highly enantioselective Michael reaction of acetone with a variety of nitroolefins catalyzed by N-[(1R,2R)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-)-thiourea (1b) together with acetic acid is described. The Michael addition products were obtained in high yields (76-94%) and Lip to 96% ee. (C) 2009 Elsevier Ltd. All rights reserved.