Synlett ( IF 1.7 ) Pub Date : 2022-03-07 , DOI: 10.1055/a-1790-3230
Wei Liu 1 , Donglei Wang 1 , Dekun Zhang 1 , Xiaoyu Yang 1
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Optically active amines represent critically important subunits in bioactive natural products and pharmaceuticals, as well as key scaffolds in chiral catalysts and ligands. Kinetic resolution of racemic amines and enantioselective desymmetrization of prochiral amines have proved to be efficient methods to access enantioenriched amines, especially when the racemic or prochiral amines were easy to prepare while the chiral ones are difficult to be accessed directly. In this Account, we systematically summarized the development of kinetic resolution and desymmetrization of amines through nonenzymatic asymmetric catalytic approaches in the last two decades.
1 Introduction
2 Kinetic Resolution of Amines
2.1 Kinetic Resolution of Amines via Asymmetric Transformations of the Amino Group
2.1.1 Asymmetric N-Acylations
2.1.2 Asymmetric N-Alkylation
2.1.3 Asymmetric N-Arylation
2.1.4 Other Asymmetric N-Functionalizations
2.1.5 Asymmetric Dehydrogenation of Amines
2.1.6 Selective C–N Bond Cleavage of Amines
2.2 Kinetic Resolution of Amines via Asymmetric Transformations without Amino Group Participating
3 Enantioselective Desymmetrization of Amines
3.1 Desymmetrization of Diamines
3.2 Desymmetrization of Prochiral Monoamines
4 Conclusion and Outlooks
中文翻译:

胺的催化动力学拆分和去对称化
光学活性胺是生物活性天然产物和药物中至关重要的亚基,也是手性催化剂和配体中的关键支架。外消旋胺的动力学拆分和前手性胺的对映选择性去对称化已被证明是获得对映体富集胺的有效方法,特别是当外消旋胺或前手性胺易于制备而手性胺难以直接获得时。在本文中,我们系统地总结了过去二十年来通过非酶不对称催化方法对胺的动力学拆分和去对称化的发展。
1 简介
2 胺的动力学拆分
2.1 通过氨基的不对称变换动力学拆分胺
2.1.1 不对称 N-酰化
2.1.2 不对称 N-烷基化
2.1.3 不对称 N-芳基化
2.1.4 其他非对称 N 函数化
2.1.5 胺的不对称脱氢
2.1.6 胺的选择性C-N键断裂
2.2 胺的动力学拆分通过没有氨基参与的不对称变换
3 胺的对映选择性去对称化
3.1 二胺的去对称化
3.2 前手性单胺的去对称化
4 结论与展望