Iterative synthesis of selectively substituted. alpha.,. beta.-unsaturated and saturated medium-ring lactones

…, G Rousseau, J Seyden-Penne

文献索引：Fouque, Elie; Rousseau, Gerard; Seyden-Penne, Jacqueline Journal of Organic Chemistry, 1990 , vol. 55, # 16 p. 4807 - 4817

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被引用次数: 27

摘要

Chloro, chloromethyl, and chlorofluoro carbenoids, generated by reaction of a base on the corresponding halides, were added to trimethylsilyl enol ethers derived from lactones, to give 1-[(trimethylsilyl) oxy]-2-chlorobicyclo-[nlO] oxanes. Thermal rearrangement of these adducts led to the a, o-ethylenic lactones, corresponding to a one-carbon ring expansion of the starting lactones. After hydrogenation, with the same iterative sequence a new one- ...