α-haloenol acetates: Versatile reactants for oxetan-2-one, azetidin-2-one and isoxazolidin-5-one synthesis

Romain Bejot, Siddam Anjaiah, J R Falck, Charles Mioskowski

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)101-107
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number1
DOIs
StatePublished - Jan 1 2007

Keywords

  • Aldol reaction
  • Aluminum
  • Heterocycles
  • Lactonization
  • Tandem reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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