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DOI: https://doi.org/10.6023/cjoc202504033

综述与进展

机械手性轮烷研究进展

  • 朱瑞卿 ,
  • 朱婷 ,
  • 王超 ,
  • 宗利利
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  • a南京工业大学化学与分子工程学院 南京 211816;
    b厦门大学药学院 厦门 361102

收稿日期: 2025-04-29

  修回日期: 2025-06-19

  网络出版日期: 2025-07-18

基金资助

国家自然科学基金(No. 21901115)资助项目.

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Research Progress in Mechanically Chiral Rotaxanes

  • Zhu Ruiqing ,
  • Zhu Ting ,
  • Wang Chao ,
  • Zong Lili
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  • aSchool of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816;
    bSchool of Pharmaceutical Sciences, Xiamen University, Xiamen 361102

Received date: 2025-04-29

  Revised date: 2025-06-19

  Online published: 2025-07-18

Supported by

National Natural Science Foundation of China (No. 21901115).

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摘要

机械手性轮烷作为机械互锁分子的重要分支,凭借机械键诱导的独特立体化学特性,在分子机器与不对称催化等领域展现出广阔应用前景. 根据组件的对称性特征,轮烷的机械手性主要分为机械面手性、机械轴手性与机械点手性三类. 本文基于非手性组件的对称面分析,组合各种类型的大环和轴体,阐述了这三类机械手性的特征. 当前,机械手性轮烷的制备主要是基于手性池和手性辅基的非对映选择性合成策略,基于手性催化剂的对映选择性催化合成机械面手性和机械点手性轮烷也有少量报道. 按轮烷的机械手性分类,本文从合成方法上对该领域现状和未来发展进行了总结与展望. 本文还简要介绍了机械手性轮烷的应用.

关键词： 轮烷; 机械面手性; 机械轴手性; 对称面; 不对称合成

本文引用格式

朱瑞卿 , 朱婷 , 王超 , 宗利利 . 机械手性轮烷研究进展[J]. 有机化学, 0 : 4033 . DOI: 10.6023/cjoc202504033

Abstract

Mechanically chiral rotaxanes, as a critical subclass of mechanically interlocked molecules (MIMs), demonstrate broad application prospects in molecular machines and asymmetric catalysis due to their unique stereochemical properties induced by mechanical bonds. Based on the symmetry feature of their components, mechanical chirality of rotaxanes is classified into three categories: mechanically planar chirality, mechanically axial chirality, and mechanical point-chirality. The stereochemical features of these three types are elucidated by analyzing the symmetry planes of each achiral macrocycle and axle, and then combining these two components. Currently, the preparation of mechanically chiral rotaxanes mainly relies on diastereoselective strategies employing chiral pools or chiral auxiliaries. A limited number of catalytic enantioselective synthesis of mechanically planar chiral and mechanically point-chiral rotaxanes have also been reported. This review systematically summarizes the current status and future directions in the field, categorized by the types of rotaxane chirality and their corresponding synthetic strategies. Application of mechanically chiral rotaxanes is also briefly introduced.

Key words： rotaxane; mechanically planar chirality; mechanically axial chirality; symmetry plane; asymmetric synthesis

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