Chiral Bifunctional Thiourea-Catalyzed Enantioselective Michael Addition of Ketones to Nitrodienes

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.