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Communication | Regular issue | Vol 32, No. 8, 1991, pp.1487-1490
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5806
An Efficient and Convenient Route to Spiro-fused γ-Butyro- and δ-Valerolactones

Fusao Kido,* Toshiya Abiko, Abul B. Kazi, Michiharu Kato, and Akira Yoshikoshi

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

Abstract

Treatment of the α-diazomalonates (5a-c) of 2-[(2-phenylthiomethyl)-1-cycloalkenyl]ethanols with rhodium acetate led to the [2,3] sigmatropic rearrangement of the cyclic allylsulfonium ylides (6a-c) to give the spiro-fused δ-valerolactones (7a-c) in excellent yields. Similarly, the spiro-fused γ-butyrolactone (10) was prepared starting with the α-diazomalonate (9) of [(2-phenylthiomethyl)-1-cyclohexenyl]methanol analog.