The Journal of Organic Chemistry

Metal-promoted cyclization. 3. Highly selective synthesis of. alpha.-alkylidenetetrahydrofurans and. gamma.-alkylidenebutyrolactones via intramolecular opening of …

FT Luo, EI Negishi

Index: Luo, Fen-Tair; Negishi, Ei-ichi Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 5144 - 5146

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Citation Number: 23

Abstract

Summary: Treatment of a-(3-hydroxypropyl)-a-(tri-methylsilyl) epoxides with KH in THF cleanly provides a-alkylidenetetrahydrofurans in high yields with 295% retention of stereochemistry, while epoxidation of y-(tri-methylsily1)-y, d-unsaturated carboxylic acids