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Communication | Regular issue | Vol 32, No. 12, 1991, pp.2315-2318
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5880
New Entry to Diastereoselective Synthesis of β,γ-Disubstituted γ-Lactones. Application to "Self-immolative" Enantioselective Synthesis of 5-Alkylbutenolides

Tsutomu Yokomatsu, Yuko Yuasa, Shinzo Kano, and Shiroshi Shibuya*

*Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Photo-initiated radical allylation of γ-phenylthio-γ-lactones (5a,b and 6b), derived from 3-hydroxy-4-(phenylthio)butyrates, gave trans β-oxygenated γ-allyl-γ-lactones (7a,b) in high degree of diastereoselectivity. The method was applied to enantioselective synthesis of (R)-5-(2-hydroxyethyl)-2,5-dihydro-2-furanone (11) with high optical purity.