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α-Haloenol Acetates: Versatile Reactants for Oxetan-2-one, Azetidin-2-one and Isoxazolidin-5-one Synthesis

✍ Scribed by Romain Bejot; Siddam Anjaiah; J. R. Falck; Charles Mioskowski

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 152 KB
Volume: 2007
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200600708

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✦ Synopsis

Abstract

New ketene equivalents, namely α‐haloenol acetates, are investigated as both nucleophilic and electrophilic reactants in a tandem aldol–lactonization reaction. Diethylaluminum ethoxide proves to be an efficient promoter for the aldol reaction with a wide range of substrates, including inter alia, aldehydes, ketones, imines, nitrones and oximes, leading to oxetan‐2‐ones, azetidin‐2‐ones and isoxazolidin‐5‐ones. The resultant heterocyclic adducts are common structural elements in numerous compounds of interest as well as key intermediates in the preparation of other functionalities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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