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2016 , Vol. 36 >Issue 6: 1229 - 1240

DOI: https://doi.org/10.6023/cjoc201510024

综述与进展

基于吲哚-3-基甲醇不对称合成光学活性吲哚衍生物研究进展

  • 朱帅 ,
  • 徐鲁斌 ,
  • 王亮 ,
  • 肖建
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  • a 荆楚理工学院药物合成与优化湖北省重点实验室荆门 448000;
    b 青岛农业大学化学与药学院青岛 266109

收稿日期: 2015-10-21

  修回日期: 2015-12-15

  网络出版日期: 2016-02-01

基金资助

荆楚理工学院药物合成与优化湖北省重点实验室开放基金(Nos.OPP2015YB01,OPP2015ZD02)、青岛农业大学高层次人才启动基金(Nos.6631112323,6631115015)资助项目.

收起

Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols

  • Zhu Shuai ,
  • Xu Lubin ,
  • Wang Liang ,
  • Xiao Jian
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  • aHubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen 448000;
    b College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109

Received date: 2015-10-21

  Revised date: 2015-12-15

  Online published: 2016-02-01

Supported by

Project supported by the Open Project Program of Hubei Key Laboratory of Drug Synthesis and Optimization Jingchu University of Technology (Nos. OPP2015YB01, OPP2015ZD02), the Talents of High Level Scientific Research Foundation of Qingdao Agricultural University (Nos. 6631112323, 6631115015).

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摘要

吲哚-3-基甲醇在酸作用下原位生成亲电性的类乙烯基亚胺(离子)中间体, 然后在手性催化剂催化下被亲核试剂进攻生成具有潜在生物活性的光学活性3-取代吲哚衍生物. 综述了吲哚-3-基甲醇不对称烷基化反应、不对称还原反应以及不对称重排反应合成光学活性3-取代吲哚衍生物的研究进展.

关键词： 吲哚-3-基甲醇; 光学活性; 吲哚衍生物; 不对称合成

本文引用格式

朱帅 , 徐鲁斌 , 王亮 , 肖建 . 基于吲哚-3-基甲醇不对称合成光学活性吲哚衍生物研究进展[J]. 有机化学, 2016 , 36(6) : 1229 -1240 . DOI: 10.6023/cjoc201510024

Abstract

The electrophilic intermediate, vinylogous imine or vinylogous iminium, can be in situ generated from 3-indolyl- methanols under acidic conditions. With the aid of chiral catalysts, miscellaneous nucleophiles can attack these electrophilic intermediates to afford enantioenriched and biologically important 3-substituted indole derivatives. The recent advances of preparation of optically active indole derivatives from 3-indolylmethanols via asymmetric alkylation, asymmetric reduction and asymmetric rearrangement are summarized.

Key words： 3-indolylmethanol; optically active; indole derivatives; asymmetric synthesis

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