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

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• 作者：Chengwei Liu ; Marcel Achtenhagen ; Michal Szostak
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2375-2378
• 全文大小：417K
• 年卷期：0
• ISSN：1523-7052

文摘

A general and highly chemoselective method for the synthesis of ketones by the addition of organometallics to N-acylazetidines via stable tetrahedral intermediates is reported for the first time. The transformation is characterized by its wide substrate scope and exquisite selectivity for the ketone products even when a large excess of nucleophilic reagents is used. Even of broader interest is the use of N-acylazetidines as bench-stable, readily available amide acylating reagents, in which the reactivity is controlled by amide pyramidalization and strain of the four-membered ring to afford synthetically valuable building blocks.