Catalytic Chemoselective Conjugate Addition of Amino Alcohols to α,β-Unsaturated Ester: Hydroxy Group over Amino Group and Conjugate Addition over Transesterification.

Abstract

A highly chemoselective conjugate addition of amino alcohols to α,β-unsaturated ester using a soft Lewis acid/hard Brønsted base cooperative catalyst was developed. This catalysis achieved chemoselective addition of a hydroxy group over an amino group. Moreover, soft metal alkoxide generation enabled chemoselective soft conjugate addition over hard transesterification. Various amino alcohols, including unprecedented cyclic β-amino alcohol, were applicable to the present catalysis.