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
