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2021 , Vol. 41 >Issue 3: 1187 - 1192

DOI: https://doi.org/10.6023/cjoc202009023

研究论文

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 ,
  • 吴昊 ,
  • 张伟鑫 ,
  • 王黎明 ,
  • 金瑛
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  • 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
† 共同第一作者

收稿日期: 2020-09-09

  修回日期: 2020-10-19

  网络出版日期: 2020-11-12

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)

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

  • Junwei Zhang ,
  • Hao Wu ,
  • Weixin Zhang ,
  • Liming Wang ,
  • Ying Jin
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  • a Department of Pharmacy, Jilin Medical University, Jilin, Jilin 132013
    b Department of Pharmacy, Yanbian University, Yanjin, Jilin 133000
* Corresponding authors. E-mail: ;
† These authors contributed equally to this work

Received date: 2020-09-09

  Revised date: 2020-10-19

  Online published: 2020-11-12

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)

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摘要

金鸡纳硅醚衍生物用于有机催化不同吲哚和靛红的不对称Friedel-Crafts反应. 筛选出最佳的催化剂体系, 以78%~96%的产率和最高达99%的对映选择性获得了手性3-羟基-2-吲哚酮. 拓宽了该反应的催化剂类型和底物范围.

关键词： 金鸡纳硅醚衍生物; 有机催化; 靛红; 吲哚; 不对称Friedel-Crafts反应

本文引用格式

张俊伟 , 吴昊 , 张伟鑫 , 王黎明 , 金瑛 . 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[J]. 有机化学, 2021 , 41(3) : 1187 -1192 . DOI: 10.6023/cjoc202009023

Abstract

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

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