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   

  1. 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 出版日期:2020-01-25 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 Jinghuaa, Geng Weishenga, Cao Shixuana, He Zhengjiea,b   

  1. 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 Online:2020-01-25 Published:2019-09-25
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21472096, J1103306).

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