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A Versatile Preparation of α,β-Unsaturated Lactones from Homoallylic Alcohols

Gary E. Keck, Xiang-Yi Li and Chad E. Knutson

*Department of Chemistry, UniVersity of Utah, 315 South 1400 East RM Dock, Salt Lake City, Utah 84112-0850, Email:

G. E. Keck, X.-Y. Li, C. E. Knutson, Org. Lett., 1999, 1, 411-413.

DOI: 10.1021/ol990632u

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The synthesis of α,β-unsaturated lactones from β-acetoxy aldehydes is achieved by reaction with the lithium enolate of methyl acetate. The reaction is relatively insensitive to structural changes in the aldehyde substrates. The process was extended to the synthesis of five-ring lactones from α-acetoxy aldehydes.

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proposed mechanism

Key Words

5,6-dihydropyran-2-ones, ozone

ID: J54-Y1999