Chiral β-Keto Propargylamine Synthesis via Enantioselective Mannich Reaction of Enamides with C-Alkynyl N-Boc N,O-Acetals

Fang-Fang Feng, Shen Li, Chi Wai Cheung* and Jun-An Ma*

*Department of Chemistry, Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, P.R. China, Email: zhiwei.zhangtju.edu.cn, majun_an68tju.edu.cn

F.-F. Feng, S. Li, C. W. Cheung, J.-A. Ma, Org. Lett., 2019, 21, 8419-8423.

DOI: 10.1021/acs.orglett.9b03181

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Abstract

A streamlined and general enantioselective Mannich reaction of enamides with C-alkynyl N-Boc N,O-acetals, which serve as readily available C-alkynyl imine precursors, provides a range of chiral β-keto N-Boc-propargylamines in high yields and in high enantioselectivities.

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proposed mechanism and transition-state model

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Key Words

β-amino ketones, organocatalysis

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ID: J54-Y2019