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DOI: https://doi.org/10.6023/cjoc202507009

研究论文

NHC催化[3+2]环加成反应高非对映选择性地构建环戊酮-螺环氧化吲哚化合物

  • 高源 ,
  • 刘岩 ,
  • 李师伍 ,
  • 唐天胜 ,
  • 孟钰坤 ,
  • 赵志飞
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  • 石河子大学化学化工学院/化工绿色过程省部共建国家重点实验室培育基地 新疆石河子 832000

收稿日期: 2025-07-08

  修回日期: 2025-10-09

  网络出版日期: 2025-11-27

基金资助

新疆维吾尔自治区“天池英才”青年博士项目 (No. CZ002737) 和石河子大学 (No. 2022ZK003) 资助项目.

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N-Heterocyclic Carbene-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes

  • Gao Yuan ,
  • Liu Yan ,
  • Li Shiwu ,
  • Tang Tiansheng ,
  • Meng Yukun ,
  • Zhao Zhifei
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  • School School of Chemistry and Chemical Engineering, Shihezi University/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering Shihezi, Xinjiang 832000

Received date: 2025-07-08

  Revised date: 2025-10-09

  Online published: 2025-11-27

Supported by

Tianchi Talent Project of Xinjiang Uygur Autonomous Region (No. CZ002737) and Shihezi University (No. 2022ZK003)

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摘要

在氮杂环卡宾(NHC)催化下, α,β-不饱和醛与3-烯基氧化吲哚化合物经过[3+2]环加成反应高效合成含一个螺碳中心的连续三个立体中心的环戊酮-螺环氧化吲哚. 该反应具有良好的底物普适性,获得了中等到良好的产率 (43%-78%) 和优异的非对映选择性(> 20:1 dr). 此外,反应还具有反应条件温和, 操作简便的优点,并且克级反应也能顺利进行. 该研究为高效构建官能团化的环戊酮-螺环氧化吲哚化合物提供了新的合成方法学.

关键词： 氮杂环卡宾; 环加成; 3-烯基氧化吲哚; 环戊酮-螺环氧化吲哚

本文引用格式

高源 , 刘岩 , 李师伍 , 唐天胜 , 孟钰坤 , 赵志飞 . NHC催化[3+2]环加成反应高非对映选择性地构建环戊酮-螺环氧化吲哚化合物[J]. 有机化学, 0 : 7009 . DOI: 10.6023/cjoc202507009

Abstract

Under N-heterocyclic carbene (NHC) catalysis, a [3+2] cycloaddition reaction between α,β-unsaturated aldehydes and 3-alkenyl oxindoles efficiently constructs spirooxindole-fused cyclopentanes derivatives with three contiguous stereocenters including one spirocarbon center. This transformation demonstrates broad substrate scope, delivering products with moderate to good yields (43%-78%) and excellent diastereoselectivity (>20:1 dr). The protocol features mild reaction conditions, operational simplicity, and scalability to gram-level synthesis. This study establishes a novel synthetic methodology for the efficient construction of functionalized spirooxindole-fused cyclopentanes.

Key words： N-heterocyclic carbene; cycloaddition; 3-alkenyl oxindole; spirooxindole-fused cyclopentanes

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