Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones

doi:10.6023/cjoc201908034

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 40-52.DOI: 10.6023/cjoc201908034 Previous Articles Next Articles

基于α-溴代酮的催化不对称合成3,3-螺环丙基吲哚酮和乙烯基环丙烷

罗京华^a, 耿玮笙^a, 曹仕轩^a, 贺峥杰^a,b

a 南开大学化学学院元素有机化学国家重点实验室天津 300071;
b 天津化学化工协同创新中心天津 300071

收稿日期:2019-08-26 修回日期:2019-09-20 发布日期:2019-09-25
通讯作者: 贺峥杰 E-mail:zhengjiehe@nankai.edu.cn
基金资助:
国家自然科学基金（Nos.21472096，J1103306）资助项目.

Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones

Luo Jinghua^a, Geng Weisheng^a, Cao Shixuan^a, He Zhengjie^a,b

a State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071;
b Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300071

Received:2019-08-26 Revised:2019-09-20 Published:2019-09-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21472096, J1103306).

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Abstract

Under the catalysis of chiral amine methylated quinidine, highly diastereo-and enantioselective cyclopropanation reactions of α-bromoketones with 3-(substituted methylene) oxindoles and electron-deficient 1,3-dienes have been realized respectively, providing corresponding functionalized 3,3-spirocyclopropyl oxindoles and vinylcyclopropanes in 46%~99% yields with up to 98% ee and up to 20:1 dr. Thus, a facile and complementary synthetic method for chiral title compounds is successfully develped by the catalytic ammonium ylide strategy.

Key words: chiral amine, [2+1] annulation reaction, α-bromoketone, asymmetric synthesis

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Luo Jinghua, Geng Weisheng, Cao Shixuan, He Zhengjie. Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 40-52.

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基于α-溴代酮的催化不对称合成3,3-螺环丙基吲哚酮和乙烯基环丙烷

Catalytic Enantioselective Syntheses of Functionalized 3,3-Spirocyclopropyl Oxindoles and Vinylcyclopropanes via Ammonium Ylides Generated from α-Bromoketones

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