有机化学 ›› 2025, Vol. 45 ›› Issue (8): 2637-2659.DOI: 10.6023/cjoc202502011 上一篇    下一篇

综述与进展

α,β-不饱和γ-内酯(酰胺)的不对称催化合成

沈健a,b,, 王彦博b,, 吴正兴b,*(), 徐德锋a,*(), 张万斌b   

  1. a 常州大学石油化工学院 药学院 江苏常州 213164
    b 上海交通大学化学化工学院 上海市手性药物分子工程重点实验室 上海 200240
  • 收稿日期:2025-02-14 修回日期:2025-03-23 发布日期:2025-04-16
  • 作者简介:

    †共同第一作者.

  • 基金资助:
    国家自然科学基金(22471162); 郑州上海交大产业技术研究院(ZZHC-2024-001); 江苏省常州市社会发展重点研究计划(CE20205058)

Asymmetric Catalytic Synthesis of α,β-Unsaturated γ-Lactone and γ-Lactam

Jian Shena,b, Yanbo Wangb, Zhengxing Wub,*(), Defeng Xua,*(), Wanbin Zhangb   

  1. a School of Petrochemical Engineering, School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164
    b Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2025-02-14 Revised:2025-03-23 Published:2025-04-16
  • Contact: *E-mail:markxu@cczu.edu.cn;wzxtheway@sjtu.edu.cn
  • About author:

    †The authors contributed equally to this work.

  • Supported by:
    National Natural Science Foundation of China(22471162); Zhengzhou Industrial Technology Research Institute of Shanghai Jiao Tong University(ZZHC-2024-001); Key Research Plan for Social Development in Changzhou, Jiangsu Province(CE20205058)

光学活性的α,β-不饱和γ-内酯(酰胺)是许多天然产物的核心骨架. 这些天然产物表现出广泛的生物活性, 对于开发新型药物具有重要意义. 同时, 光学活性的α,β-不饱和γ-内酯(酰胺)作为一类重要的手性砌块, 在合成多种生物活性分子和复杂分子中发挥了重要作用. 鉴于其广泛的生物活性及可以多样化修饰的特点, 构建此类结构的不对称催化合成方法受到学术界的广泛关注. 此综述概述了利用过渡金属催化剂、路易斯酸催化剂及有机小分子催化剂合成α,β-不饱和γ-内酯(酰胺)的不对称催化合成方法, 探讨了代表性反应中的立体控制机制及其应用价值.

关键词: α,β-不饱和γ-内酯, α,β-不饱和γ-内酰胺, 不对称催化

Optically active α,β-unsaturated γ-lactone and γ-lactam serve as core scaffolds in numerous natural products. These natural products exhibit a broad spectrum of bioactivities, making them highly significant for the development of novel drugs. Furthermore, as an important class of chiral building blocks, optically active α,β-unsaturated γ-lactone and γ-lactam play a pivotal role in synthesizing diverse bioactive compounds and complex molecules. Given their versatile biological activities and potential for structural diversification, the construction of such frameworks via asymmetric catalytic synthesis has received much attention from the academic community. This review summarizes the recent advances in asymmetric catalytic methods for synthesizing α,β-unsaturated γ-lactone and γ-lactam employing transition metal catalyst, Lewis acid catalyst and organo- catalyst, and discusses the stereocontrol mechanism in representative examples and the related application value.

Key words: α,β-unsaturated γ-lactone, α,β-unsaturated γ-lactam, asymmetric catalysis