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2023 , Vol. 43 >Issue 8: 2864 - 2877

DOI: https://doi.org/10.6023/cjoc202302017

研究论文

钯催化不对称[3＋4]环加成构建吲哚并环庚烷

  • 王熠 ,
  • 张键 ,
  • 刘飏子 ,
  • 罗晓燕 ,
  • 邓卫平
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  • a 华东理工大学药学院 上海 200237
    b 浙江师范大学化学与材料科学学院 浙江金华 321004

收稿日期: 2023-02-25

  修回日期: 2023-04-04

  网络出版日期: 2023-04-23

基金资助

国家重点研发计划(2021YFA0804900); 国家自然科学基金(21971062); 国家自然科学基金(22171082); 上海细胞代谢光遗传学技术前沿科学研究基地资助项目

收起

Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles

  • Yi Wang ,
  • Jian Zhang ,
  • Yangzi Liu ,
  • Xiaoyan Luo ,
  • Weiping Deng
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  • a School of Pharmacy, East China University of Science and Technology, Shanghai 200237
    b College of Chemistry, Zhejiang Normal University, Jinhua 321004
*E-mail: ;

Received date: 2023-02-25

  Revised date: 2023-04-04

  Online published: 2023-04-23

Supported by

The National Key Research and Development Program of China(2021YFA0804900); The National Natural Science Foundation of China(21971062); The National Natural Science Foundation of China(22171082); The Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism

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摘要

报道了一种通过钯催化的脱羧方法, 能够以较好的收率、中等至优异的对映选择性, 以及良好的非对映选择性高效地合成吲哚并环庚烷类化合物. 在该方法中, 乙烯基吲哚噁唑酮被钯催化剂活化脱羧形成两性离子中间体, 接着被缺电子双烯所捕获发生不对称[3＋4]环加成反应.

关键词： 脱羧; 吲哚并环庚烷; 不对称; 环加成

本文引用格式

王熠 , 张键 , 刘飏子 , 罗晓燕 , 邓卫平 . 钯催化不对称[3＋4]环加成构建吲哚并环庚烷[J]. 有机化学, 2023 , 43(8) : 2864 -2877 . DOI: 10.6023/cjoc202302017

Abstract

A Pd-catalyzed decarboxylation strategy for the efficient synthesis of cyclohepta[b]indoles in good yields with good to excellent enantioselectivities and moderate diastereoselectivities is reported. In this procedure, viny indoloxazolidones were activated by Pd catalyst to generate zwitterionic intermediates in situ, which were then trapped by the electro-deficient diene species via the asymmetric [3＋4] cycloaddition process.

Key words： decarboxylation; cyclohepta[b]indoles; asymmetric; cycloadditions

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