有机化学 ›› 2022, Vol. 42 ›› Issue (10): 3373-3381.DOI: 10.6023/cjoc202209002 上一篇    下一篇

所属专题: 不对称催化专辑

研究论文

钯/新型轴手性膦-烯配体催化的吲哚不对称烯丙基烷基化反应

贾仕虎a, 陈思元a, 刘泽水a,b, 程鸿刚a,*(), 周强辉a,c,*()   

  1. a 武汉大学化学与分子科学学院 武汉 430072
    b 郑州大学化学学院 绿色催化中心 郑州 450001
    c 武汉大学高等研究院 武汉 430072
  • 收稿日期:2022-09-01 修回日期:2022-10-11 发布日期:2022-11-02
  • 通讯作者: 程鸿刚, 周强辉
  • 基金资助:
    国家自然科学基金(21871213); 国家自然科学基金(22071189); 中央大学基础研究基金(2042021kf0214)

Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles

Shihu Jiaa, Siyuan Chena, Zeshui Liua,b, Honggang Chenga(), Qianghui Zhoua,c()   

  1. a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
    b Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001
    c The Institute for Advanced Studies, Wuhan University, Wuhan 430072
  • Received:2022-09-01 Revised:2022-10-11 Published:2022-11-02
  • Contact: Honggang Cheng, Qianghui Zhou
  • Supported by:
    National Natural Science Foundation of China(21871213); National Natural Science Foundation of China(22071189); Fundamental Research Funds for Central Universities(2042021kf0214)

基于两步模块化合成, 制备了一类新型的联芳基轴手性膦-烯配体. 该类配体在钯催化的吲哚不对称烯丙基烷基化反应中表现出很好的催化活性和不对称诱导效果. 在最优的反应条件下, 能以高达95%的收率和96%的对映选择性生成一系列手性的烯丙基吲哚化合物.

关键词: 钯催化, 膦-烯配体, 吲哚, 烯丙基烷基化, 不对称催化

A new type of axially chiral phosphine-alkene ligands have been developed via a two-step modular synthesis for Pd-catalyzed asymmetric allylic alkylation of indoles. Under optimized reaction conditions, a series of chiral allylindole products were obtained in generally high yields (up to 95%) and excellent enantioselectivities (up to 96% ee).

Key words: palladium catalysis, phosphine-alkene ligand, indole, allylic alkylation, asymmetric catalysis