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Chemoselective Ketone Synthesis by the Addition of Organometallics to N-Acylazetidines

Chengwei Liu, Marcel Achtenhagen and Michal Szostak*

*Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States, Email: michal.szostakrutgers.edu

C. Liu, M. Achtenhagen, M. Szostak, Org. Lett., 2016, 18, 2375-2378.

DOI: 10.1021/acs.orglett.6b00842 (free Supporting Information)


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Abstract

N-acylazetidines are bench-stable, readily available amide acylating reagents, in which the reactivity is controlled by amide pyramidalization and strain of the four-membered ring. A general and highly chemoselective synthesis of ketones by the addition of organometallics to N-acylazetidines via stable tetrahedral intermediates offers wide substrate scope and exquisite selectivity for the ketone products.

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Key Words

ketones, aryl ketones


ID: J54-Y2016