Citation: 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. doi: 10.6023/cjoc201908034 shu

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

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

Corresponding author: He Zhengjie, zhengjiehe@nankai.edu.cn
Received Date: 26 August 2019
Revised Date: 20 September 2019
Available Online: 25 January 2019
Fund Project: the National Natural Science Foundation of China 21472096the National Natural Science Foundation of China J1103306Project supported by the National Natural Science Foundation of China (Nos. 21472096, J1103306)

Figures(1)

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.
- chiral amine,
- [2+1] annulation reaction,
- α-bromoketone,
- 1symmetric synthesis
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