Catalytic Kinetic Resolution and Desymmetrization of Amines

Abstract

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

Key words

chiral amines - kinetic resolution - enantioselective desymmetrization - asymmetric catalysis

Publication History

Received: 18 January 2022

Accepted after revision: 07 March 2022

Accepted Manuscript online:
07 March 2022

Article published online:
13 April 2022

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