铜（I）催化的活性亚甲基化合物与卤代乙烯的分子内碳-碳偶联反应：功能化亚烷基环丁烷的高效合成

Cu(I)-catalyzed intramolecular C-C coupling of activated methylene compounds with vinyl halides: efficient synthesis of functionalized alkylidenecyclobutanes.

作者信息

Chen Liqun, Shi Min, Li Chaozhong

机构信息

School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai, PR China.

出版信息

Org Lett. 2008 Nov 20;10(22):5285-8. doi: 10.1021/ol802012q. Epub 2008 Oct 16.

DOI:10.1021/ol802012q

PMID:18922006

Abstract

With the catalysis of CuI/L-proline, a number of 2-(3-bromobut-3-enyl)malonates underwent efficient intramolecular C-vinylation leading to the synthesis of functionalized alkylidenecyclobutanes. Competition experiments revealed that this four-membered ring closure is fundamentally preferred over the corresponding five-membered ring closure.

摘要

在碘化亚铜/ L-脯氨酸的催化作用下，许多2-(3-溴丁-3-烯基)丙二酸酯发生了高效的分子内C-乙烯基化反应，从而合成了官能化的亚烷基环丁烷。竞争实验表明，这种四元环的闭环反应从根本上比相应的五元环闭环反应更受青睐。