Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3065-3077.DOI: 10.6023/cjoc202005020 Previous Articles     Next Articles

Special Issue: 黄乃正院士七十华诞专辑


王才a, 周锋a, 周剑a,b   

  1. a 华东师范大学化学与分子工程学院 绿色化学与化工过程绿色化上海市重点实验室 上海 200062;
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
  • 收稿日期:2020-05-09 修回日期:2020-05-28 发布日期:2020-06-10
  • 通讯作者: 周锋, 周剑;
  • 基金资助:

Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction

Wang Caia, Zhou Fenga, Zhou Jiana,b   

  1. a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2020-05-09 Revised:2020-05-28 Published:2020-06-10
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21672068, 21871090).

As one of the most important click reactions, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) has found widespread applications. Nevertheless, the exploitation of enantioselective CuAAC remains largely undeveloped. Although the reaction itself does not generate chiral elements, the enantioselective CuAAC can be realized via the desymmetrization of prochiral dialkynes or diazides, as well as the kinetic resolution of racemic azides or terminal alkynes. Notably, enantioselective CuAAC provides efficient access to structurally diverse enantioenriched compounds featuring an azide, terminal alkyne or 1,4-disubstituted 1,2,3-triazoles, which are valuable structural units in organic synthesis or medicinal chemistry. Since the first highly enantioselective CuAAC reaction via desymmetrization of prochiral diynes was reported in 2013, substantial progress has been made in this research area. To date, enantioselective CuAAC has been successfully applied to the construction of central chirality, axial chirality and planar chirality. The recent exciting achievements are summarized, the challenges in this context are briefly discussed, and the synthetic opportunities for future development are outlined.

Key words: copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, desymmetrization, (dynamic) kinetic resolution