A Practical and Efficient Method for the Synthesis of β-Lactones

Article abstract of DOI:10.1021/jo00003a047

This paper describes a convenient one-step preparation of β-lactames based on the addition of thiol ester enolates to carbonyl compounds.Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce β-lactones in good to excellent yield.The new β-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns.In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded β-lactone diasteromers, and in some cases the reaction proceeds with excellent stereoselectivity.In conjunction with the stereospecific decarboxylation of β-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.