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

A highly chemoselective conjugate addition of amino alcohols to alpha,beta-unsaturated ester using a soft Lewis acid/hard Bronsted 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 beta-amino alcohol, were applicable to the present catalysis.