A Recyclable Fluorous (<i>S</i>)-Pyrrolidine Sulfonamide Promoted Direct, Highly Enantioselective Michael Addition of Ketones and Aldehydes to Nitroolefins in Water

Abstract

[reaction: see text] A recycle and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to six cycles) without a significant loss of catalytic activity and stereoselectivity.