有机化学 ›› 2020, Vol. 40 ›› Issue (3): 575-588.DOI: 10.6023/cjoc201910010 上一篇    下一篇

综述与进展

胺及其衍生物的非酰基化动力学拆分

唐亮, 李雪薇, 谢芳, 张万斌   

  1. 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:2019-10-10 修回日期:2019-11-11 发布日期:2020-04-02
  • 通讯作者: 谢芳 E-mail:xiefang@sjtu.edu.cn
  • 基金资助:
    国家自然科学基金(No.21572129)资助项目.

Catalytic Kinetic Resolution of Amines and Their Derivatives by Non-acylation Reaction

Tang Liang, Li Xuewei, Xie Fang, Zhang Wanbin   

  1. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2019-10-10 Revised:2019-11-11 Published:2020-04-02
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21572129).

光学纯胺在合成与药物化学领域都有着广泛的应用,发展其高效的合成方法一直以来是有机化学界的研究热点.其中通过N酰基化及去酰基化动力学拆分方法获得光学纯胺化合物,已经成为合成手性胺类化合物的重要方法.近年来,基于非酰基化(或去酰基化)的不对称反应实现外消旋胺的动力学拆分的报道不断涌现,包括一些氨基不参与反应的非酰基化(或去酰基化)不对称反应的外消旋胺的动力学拆分.根据氮原子是否参与反应以及反应类型的不同,总结了外消旋胺的化学催化动力学拆分的研究进展.

关键词: 光学纯胺, 动力学拆分, 非酶催化, 非酰基化(去酰基化), 不对称催化反应

Enantiopure amines are important building blocks with a plethora of applications in the fields of medicine, agriculture and materials. Kinetic resolution (KR) of racemic amines is one of the most important methods for obtaining enantiopure amines. However, KR of amines is little investigated because of their high reactivity and coordinating ability in the corresponding KR of alcohols. Till now, major developments using non-enzymatic catalysts for KR of amines have been extensively achieved by catalytic acylation (or deacylation). Only recently the non-acylation KR of amines is improving. The relatively wide range of different catalytic asymmetric reactions have been employed as strategies for the efficient KR of amines. For some cases, the asymmetric reactions do not involve with nitrogen atoms of racemic substrates. This review aims to introduce the development of the non-acylation KR of amines for the synthesis of enantiopure amines.

Key words: enantiopure amines, kinetic resolution, nonenzymatic, non-acylation, catalytic asymmetric reactions