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DOI: https://doi.org/10.6023/cjoc202602006

研究论文

铱催化不对称串联烯丙基化/iso-Pictet-Spengler环化反应合成手性四氢-γ-咔啉

  • 黄锦龙 ,
  • 肖帆 ,
  • 吴慧敏 ,
  • 董秀琴 ,
  • 王春江
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  • a武汉大学化学与分子科学学院 基础科学-化学湖北省研究中心 武汉 430072 中国;
    b中国科学院上海有机化学研究所金属有机化学全国重点实验室 上海 200032 中国
†共同第一作者

收稿日期: 2026-02-03

  修回日期: 2026-03-19

  网络出版日期: 2026-04-03

基金资助

国家重点研发计划项目(No. 2023YFA1506700), 中央高校基本科研业务费专项资金项目(2042025kf0032)和国家自然科学基金(No. 22271226和22371216).

收起

Access to Chiral Tetrahydro-γ-carbolines via Iridium-Catalyzed Asymmetric Cascade Allylation/iso-Pictet-Spengler Cyclization

  • Jin-Long Huang ,
  • Fan Xiao ,
  • Hui-Min Wu ,
  • Xiu-Qin Dong ,
  • Chun-Jiang Wang
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  • aHubei Research Center of Fundamental Science-Chemistry, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China;
    bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 230021, People’s Republic of China
†(These authors contributed equally to this work).

Received date: 2026-02-03

  Revised date: 2026-03-19

  Online published: 2026-04-03

Supported by

Project supported by the National Key R&D Program of China (2023YFA1506700), the Fundamental Research Funds for the Central Universities (2042025kf0032), and the Natural Science Foundation of China (No. 22271226 and 22371216).

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摘要

本文发展了一种高效、高立体选择性的合成方法，成功构建了具有多个立体中心的手性四氢-γ-咔啉类化合物。通过铱催化亚胺基丙二酸酯与方便易得的吲哚基烯丙醇之间的不对称串联烯丙基化/iso-Pictet-Spengler环化反应，在路易斯酸Zn(OTf)₂促进下进行。通过该方法能获得一系列含有两个非相邻手性中心的手性四氢-γ-咔啉衍生物，产率中等至良好（50%-80%），并表现出优异的立体控制水平（>20:1 dr, 96%->99% ee）。该策略具有高原子经济性，反应生成的水作为副产物。

关键词： 不对称催化串联反应; 不对称烯丙基化; iso-Pictet-Spengler环化反应; 铱催化; 手性四氢-γ-咔啉

本文引用格式

黄锦龙 , 肖帆 , 吴慧敏 , 董秀琴 , 王春江 . 铱催化不对称串联烯丙基化/iso-Pictet-Spengler环化反应合成手性四氢-γ-咔啉[J]. 有机化学, 0 : 202602006 -202602006 . DOI: 10.6023/cjoc202602006

Abstract

An efficient and highly stereoselective protocol has been developed for the construction of chiral tetrahydro-γ-carbolines bearing two non-adjacent stereocenters via an iridium-catalyzed asymmetric cascade allylation/iso-Pictet-Spengler cyclization between iminomalonates and readily accessible indolyl allylic alcohols with Lewis acid Zn(OTf)₂ as the promoter. A broad range of chiral tetrahydro-γ-carboline derivatives containing two non-adjacent stereocenters could be obtained in moderate to good yields (50%-80%) with excellent stereocontrol (>20:1 dr, 96%->99% ee). This protocol features high atom economy, generating water as the sole byproduct.

Key words： Asymmetric catalytic cascade reaction; Asymmetric allylation; iso-Pictet-Spengler cyclization; Iridium catalysis; Chiral tetrahydro-γ-carbolines;

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