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Paper | Special issue | Vol 33, No. 2, 1992, pp.607-618
Published online, 1st January, 1970
DOI: 10.3987/COM-91-S55
An Efficient Synthetic Route to γ,δ-Unsaturated Seven-memberd Lactones

Fusao Kido, Abul B. Kazi, Kazuo Yamaji, Michiharu Kato,* and Akira Yoshikoshi

*Institute for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku, Sendai 980-8577, Japan

Abstract

Treatment of the diazomalonates (9a-d) of 2-phenylthio-3-butenol derivatives with catalytic rhodium acetate resulted in the [2,3]sigmatropic rearrangement of six-membered allylsulfonium ylides to provide γ, δ-unsaturated seven-membered lactones (10a-d) in good yields.