1009-14-9 Chemoselective Ketone Synthesis by the Addition of Organometallics to N-Acylazetidines

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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. https://www.lookchem.com/CASDataBase_1009-14-9.htm

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