☆ 4.8 Article

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

ORGANIC LETTERS (2019)

期刊

ORGANIC LETTERS

卷 21, 期 20, 页码 8419-8423

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.9b03181

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Chemistry, Organic

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National Natural Science Foundation of China [21532008, 21772142, 21901181, 21971186]
Tianjin University

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Propargylamines are an important class of compounds in organic synthesis and drug discovery, yet the synthesis of chiral beta-keto propargylamines remains underdeveloped. Herein, we describe 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, to access a broad range of chiral beta-keto N-Boc-propargylamines bearing single stereogenic centers in high yields (up to 98%) and in high enantioselectivities (up to 95% ee).

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