Synthesis of Azepane Derivatives via Formal 1,3-Migration of Hydroxy and Acyloxy Groups and Selective Annulation.

Org Lett

Department of Chemistry, Key Laboratory of Surface and Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Xiasha West Higher Education District, Hangzhou, Zhejiang 310018, China.

Published: July 2022


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Article Abstract

Formal 1,3-migration of hydroxy and acyloxy groups initiated by α-imino rhodium carbene was achieved, and the following selective annulations of the corresponding zwitterions could efficiently afford azepane derivatives. Benefiting from a time-saving procedure as well as a good functional group tolerance, this unique migration-annulation protocol could provide an efficient tool for synthesizing seven-membered -heterocycles. The plausible mechanism is discussed.

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http://dx.doi.org/10.1021/acs.orglett.2c01646DOI Listing

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