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

Zhao Li; Masamichi Tamura; Ryo Yazaki; Takashi Ohshima

doi:10.1248/cpb.c16-00333

Current Topics: Communications to the Editor

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

Zhao Li, Masamichi Tamura, Ryo Yazaki, Takashi Ohshima

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Keywords: chemoselective catalysis, amino alcohol, α,β-unsaturated ester, cooperative catalyst, soft metal alkoxide

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Supplementary material

2017 Volume 65 Issue 1 Pages 19-21

DOI https://doi.org/10.1248/cpb.c16-00333

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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.

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