铜催化的不对称叠氮和炔烃的环加成反应的研究进展

doi:10.6023/cjoc202005020

有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3065-3077.DOI: 10.6023/cjoc202005020 上一篇下一篇

所属专题：黄乃正院士七十华诞专辑

综述与进展

铜催化的不对称叠氮和炔烃的环加成反应的研究进展

王才^a, 周锋^a, 周剑^a,b

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 E-mail:fzhou@chem.ecnu.edu.cn;jzhou@chem.ecnu.edu.cn
基金资助:
国家自然科学基金（Nos.21672068，21871090）资助项目.

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

Wang Cai^a, Zhou Feng^a, Zhou Jian^a,b

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).

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摘要/Abstract

尽管铜催化的叠氮和炔烃环加成（CuAAC）反应作为点击化学的核心反应得到广泛应用，然而其不对称催化的研究却相对滞后.反应本身虽然不产生手性元素，但是能够通过对具有潜手性的炔烃或叠氮化合物的去对称化以及外消旋叠氮或炔烃化合物的动力学拆分，来不对称催化合成手性叠氮、炔烃和三氮唑类具有重要应用价值的化合物.自2013年首例高对映选择性的CuAAC反应被报道以来，相关研究有了重要进展，并被成功用于中心手性、轴手性和平面手性的构建.概述了不对称CuAAC反应的研究进展，讨论其面临的发展难题和未来的发展空间.

关键词: 铜催化的叠氮和炔烃环加成(CuAAC)反应, 去对称化, (动态)动力学拆分

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

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王才, 周锋, 周剑. 铜催化的不对称叠氮和炔烃的环加成反应的研究进展[J]. 有机化学, 2020, 40(10): 3065-3077.

Wang Cai, Zhou Feng, Zhou Jian. Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3065-3077.

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铜催化的不对称叠氮和炔烃的环加成反应的研究进展

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

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