Highly Enantioselective Michael Addition of Ketones and an Aldehyde to Nitroalkenes Catalyzed by a Binaphthyl Sulfonimide in Water

Abstract

A binaphthyl sulfonimide organocatalyst was used to promote highly enantioselective and diastereoselective Michael addition reactions of ketones to nitroalkenes in water. In most cases, the products were obtained in good yields with excellent enantioselectivities and diastereoselectivities (93-97% ee, up to >99:1 dr). The catalyst could also be used in an asymmetric Michael addition of isobutyraldehyde to nitroalkenes to give the desired products in moderate yields and moderate enantioselectivities (up to 83% ee).