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2021 , Vol. 41 >Issue 2: 582 - 593

DOI: https://doi.org/10.6023/cjoc202006050

综述与进展

炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用

  • 余述燕 ,
  • 高丽宏 ,
  • 闫溢哲 ,
  • 尹志刚 ,
  • 商永嘉
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  • a 郑州轻工业大学材料与化学工程学院 郑州 450002
    b 郑州轻工业大学食品与生物工程学院 郑州 450002
    c 安徽师范大学功能分子固体教育部重点实验室 安徽芜湖 240001
* Corresponding authors. E-mail: ;

收稿日期: 2020-06-23

  修回日期: 2020-07-28

  网络出版日期: 2020-08-19

基金资助

国家自然科学基金(21602207); 郑州轻工业大学博士科研基金(2014BSJJ009); 郑州轻工业大学青年骨干教师(2019XGGJS010)

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Application of Cascade Reactions in the Synthesis of Sprio-hetero- cycles Initiated by Intramolecular Cyclization of Alkynols

  • Shuyan Yu ,
  • Lihong Gao ,
  • Yizhe Yan ,
  • Zhigang Yin ,
  • Yongjia Shang
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  • a College of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002
    b College of Food and Bioengineering, Zhengzhou University of Light Industry, Zhengzhou 450002
    c Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

Received date: 2020-06-23

  Revised date: 2020-07-28

  Online published: 2020-08-19

Supported by

the National Natural Science Foundation of China(21602207); the Doctoral Research Fund of Zhengzhou University of Light Industry(2014BSJJ009); the Young Backbone Teachers’ Fund of Zhengzhou University of Light Industry(2019XGGJS010)

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摘要

螺杂环化合物独特的立体结构和丰富的理化特性, 激发了研究工作者对其高效合成方法的持续关注. 炔醇在过渡金属作用下经exo-dig式分子内环化可原位形成环外烯醇醚, 其作为一类高活性的C2合成子, 能够与同时具有亲电和亲核特性的“双亲性底物”发生串联反应, 实现螺杂环骨架的快速构建. 综述了近年来炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用进展, 以期激发更多相关研究工作的设计与报道. 按照参与螺环构建的“双亲性底物”原子数目的不同进行分类, 重点阐述了反应采用的催化体系和反应机制, 分析了目前该领域存在的挑战, 并对未来的发展进行了展望.

关键词： 螺杂环; 炔醇; 串联反应; 环外烯醇醚

本文引用格式

余述燕 , 高丽宏 , 闫溢哲 , 尹志刚 , 商永嘉 . 炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用[J]. 有机化学, 2021 , 41(2) : 582 -593 . DOI: 10.6023/cjoc202006050

Abstract

Due to their unique stereoscopic structure and rich physical and chemical properties, spiro heterocyclic compounds have aroused the continuous attention of researchers on their efficient synthesis methods. The exo-cyclic enol ethers generated in situ by exo-dig cyclization of alkynols under the promotion of transition metals could serve as C2 synthons to react with various "amphiphilic substrates" through cascade reactions mode. These cascade reactions could afford spiro heterocyclic skeletons in highly efficient and direct manners. In this paper, the application progress of cascade reactions in the synthesis of sprio-heterocycles initiated by intramolecular cyclization of alkynols is reviewed, which aims to stimulate the disclosure of more related research work. These work is elaborated according to the different atom numbers of the "amphiphilic substrates" involved in the construction of the spiro framworks. The catalytic system and reaction mechanism are mainly described, the challenges in this field are analyzed, and the future development is also put forward.

Key words： sprio-heterocycles; alkynols; cascade reactions; exo-cyclic enol ether

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