Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3240-3262.DOI: 10.6023/cjoc202207034 Previous Articles     Next Articles

Special Issue: 不对称催化专辑

REVIEWS

过渡金属催化氧/氮杂环丙烷不对称开环反应的研究进展

杜青锋a, 张璐b, 高峰b,*(), 王乐a,*(), 张万斌b   

  1. a 上海工程技术大学化学化工学院 上海 201620
    b 上海交通大学化学化工学院 变革性分子前沿科学中心 上海市手性药物分子工程重点实验室 上海 200240
  • 收稿日期:2022-07-26 修回日期:2022-08-18 发布日期:2022-11-02
  • 通讯作者: 高峰, 王乐
  • 作者简介:
    †共同第一作者.
  • 基金资助:
    国家自然科学基金(21991112)

Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines

Qingfeng Dua, Lu Zhangb, Feng Gaob(), Le Wanga(), Wanbin Zhangb   

  1. a School of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
    b Shanghai Key Laboratory for Molecular Engineering and Chiral Drugs, Frontiers Science Center for Transformative Molecules Shanghai, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2022-07-26 Revised:2022-08-18 Published:2022-11-02
  • Contact: Feng Gao, Le Wang
  • About author:
    †These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(21991112)

Epoxides and aziridines are important three-membered cyclic compounds, which exhibit high reactivity due to their strong strain in molecules. The asymmetric ring-opening reactions of epoxides and aziridines catalyzed by transition metals are efficient strategies for the construction of chiral molecules containing O/N atoms. In this way, a series of chiral alcohols, chiral amines and chiral heterocycles can be constructed. The recent progress in transition metal-catalyzed asymmetric ring-opening reactions of epoxides and aziridines in the past two decades is reviewed with emphasis on the influence of the kinds of transition metal catalysts, nucleophiles, and ligands. Furthermore, the possible reaction mechanisms and applications for the asymmetric ring-opening reactions are discussed, and the future development in this field is also prospected.

Key words: transition metals catalysis, epoxide, aziridine, asymmetric ring-opening reaction, nucleophilic coupling