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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

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