Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N‐Alkyl β‐Enamino Esters with Trichlorosilane and Water

Abstract

First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).