Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1187-1192.DOI: 10.6023/cjoc202009023 Previous Articles     Next Articles

ARTICLES

金鸡纳硅醚衍生物有机催化吲哚与靛红的不对称Friedel-Crafts反应

张俊伟a,b, 吴昊a,b, 张伟鑫a, 王黎明a,*(), 金瑛a,*()   

  1. a 吉林医药学院药学院 吉林吉林 132013
    b 延边大学药学院 吉林延吉 133000
  • 收稿日期:2020-09-09 修回日期:2020-10-19 发布日期:2020-11-12
  • 通讯作者: 王黎明, 金瑛
  • 作者简介:
    † 共同第一作者
  • 基金资助:
    国家自然科学基金(21102055); 吉林省自然科学基金(20190201077JC); 吉林省卫生厅技术创新项目(2020J074); 国家大学生创新创业训练计划(201913706058)

Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative

Junwei Zhanga,b, Hao Wua,b, Weixin Zhanga, Liming Wanga,*(), Ying Jina,*()   

  1. a Department of Pharmacy, Jilin Medical University, Jilin, Jilin 132013
    b Department of Pharmacy, Yanbian University, Yanjin, Jilin 133000
  • Received:2020-09-09 Revised:2020-10-19 Published:2020-11-12
  • Contact: Liming Wang, Ying Jin
  • About author:
    * Corresponding authors. E-mail: ;
    † These authors contributed equally to this work
  • Supported by:
    National Natural Science Foundation of China(21102055); Natural Science Foundation of Jilin Province(20190201077JC); Technology Innovation Project of the Health Commission of Jilin Province(2020J074); National Students? Program for Innovation and Entrepreneurship Training(201913706058)

A series of cinchona alkaloid silyl ether derivatives have been used to catalyze the enantioselective Friedel-Crafts reaction of indoles with isatins. The resulting 3-hydroxy-2-oxindoles were obtained in good yields (78%~96%) with high enantioselectivities (up to 99% ee). The catalyst type and the substrate scope were broadened in this methodology.

Key words: cinchona alkaloid silyl ether, organocatalysis, isatin, indole, enantioselective Friedel-Crafts reaction