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.
- Aldol reaction
- Tandem reaction
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry