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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 1: 40 - 52

DOI: https://doi.org/10.6023/cjoc201908034

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

  • Luo Jinghua ,
  • Geng Weisheng ,
  • Cao Shixuan ,
  • He Zhengjie
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  • 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 date: 2019-08-26

  Revised date: 2019-09-20

  Online 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

Cite this article

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

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