Phosphazene Base-Catalyzed Intramolecular Hydroamidation of Alkenes with Amides

Junpei Matsuoka*, Yumika Fujimoto, Akari Miyawaki and Yasutomo Yamamoto*

*Faculty of Pharmaceutical Sciences, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe 610-0395, Japan, Email: jmatsuokdwc.doshisha.ac.jp, yayamamodwc.doshisha.ac.jp

J. Matsuoka, Y. Fujimoto, A. Miyawaki, Y. Yamamoto, Org. Lett., 2022, 24, 9447-9451.

DOI: 10.1021/acs.orglett.2c03870

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Abstract

A phosphazene base-catalyzed intramolecular hydroamidation of amide alkenes provides cyclic amides. The reaction using a catalytic amount of P₄-base had a good functional group tolerance and a broad substrate scope and could also be used to synthesize lactams, cyclic ureas, and oxazolidinones.

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proposed mechanism

P4-tBu

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Key Words

γ-lactams, oxazolidinones

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ID: J54-Y2022