131436-08-3Relevant academic research and scientific papers
A Practical and Efficient Method for the Synthesis of β-Lactones
Danheiser, Rick L.,Nowick, James S.
, p. 1176 - 1185 (2007/10/02)
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.
