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A Michael Addition-Asymmetric Transfer Hydrogenation One-Pot Enantioselective Tandem Process for Syntheses of Chiral γ-Secondary Amino Alcohols

Liang Wu, Ronghua Jin, Liang Li, Xiaoying Hu, Tanyu Cheng and Guohua Liu*

*Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, P. R. China, Email: ghliushnu.edu.cn

L. Wu, R. Jin, L. Li, X. Hu, T. Cheng, G. Liu, Org. Lett., 2017, 19, 3047-3050.

DOI: 10.1021/acs.orglett.7b00823 (free Supporting Information)


Abstract

An aza-Michael addition-asymmetric transfer hydrogenation tandem process provides chiral γ-secondary amino alcohols in high yields with high enantioselectivities. This one-pot tandem process involves an aza-Michael addition of aryl-substituted enones and amines to form aryl-substituted γ-secondary amino ketones, followed by a Ru-catalyzed asymmetric transfer hydrogenation.

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Time course of the aza-Michael addition-ATH



Key Words

Michael Addition, γ-amino alcohols


ID: J54-Y2017