Chiral bifunctional thiourea-catalyzed enantioselective Michael addition of ketones to nitrodienes

J Org Chem. 2010 Mar 5;75(5):1402-9. doi: 10.1021/jo901991v.

Abstract

Simple bifunctional thioureas, derived from the commercially available saccharides and chiral diamines, have been shown tunably to promote Michael-type addition of ketones to alpha,beta-gamma,delta-nitrodienes. The Michael adducts were obtained in good yields albeit with high enantioselectivites (84-99% ee). Furthermore, these products can be readily transformed into more useful molecules.