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Enantioselective Synthesis of γ-Aryl-γ-butyrolactones by Sequential Asymmetric Epoxidation, Ring Expansion, and Baeyer−Villiger Oxidation

2006; American Chemical Society; Volume: 71; Issue: 25 Linguagem: Inglês

10.1021/jo061341j

1520-6904

Bin Wang, Yu‐Mei Shen, Yian Shi,

Oxidative Organic Chemistry Reactions

This paper describes an enantioselective synthesis of γ-butyrolactones, using the N-tolyl-substituted oxazolidinone-containing ketone as catalyst and Oxone as oxidant via a sequential asymmetric epoxidation of benzylidenecyclopropanes, ring expansion, and Baeyer−Villiger oxidation. Up to 91% ee was obtained. Optically active cyclobutanones can also be obtained by suppressing the Baeyer−Villiger oxidation with use of more ketone catalyst and less Oxone.