A novel synthesis of α-methylene-γ-butyrolactones

H Saimoto, K Nishio, H Yamamoto, M Shinoda…

文献索引：Saimoto; Nishio; Yamamoto; Shinoda; Hiyama; Nozaki Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 10 p. 3093 - 3098

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被引用次数: 14

摘要

A new method is reported for constructing α-methylene-γ-butyrolactone moiety under neutral, anhydrous conditions. Olefin–dibromocarbene adducts were transformed into methyl 1-(dimethylaminomethyl) cyclopropanecarboxylates (3). Treatment of 3 with trimethylsilyl iodide followed by thermolytic distillation of the crude products gave α- methylene-γ-butyrolactones with high regio-and stereo selectivity.