Stereoselective Monoalkylation of α-Halocyclopropyllithiums. A Versatile Method for the Synthesis of α-Alkylcyclopropyl Acetates and Alkylidenecyclopropanes

K Kitatani, T Hiyama, H Nozaki

文献索引：Kitatani,K. et al. Bulletin of the Chemical Society of Japan, 1977 , vol. 50, p. 3288 - 3294

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被引用次数: 63

摘要

The title carbenoids (7 and 8) prepared by the action of butyllithium on dihalocyclopropanes are smoothly methylated with methyl iodide. The product ratio of cis-methylated product (3)/trans-methylated one (4)(or endo-methylated product (5)/exo-methylated one (6) is found to depend on the aging period of the carbenoids; thermodynamic equilibration gives almost 3 or 5. This procedure has been extended to general alkylation by utilizing HMPA co- ...