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Synlett 2022; 33(18): 1788-1812
DOI: 10.1055/a-1790-3230
DOI: 10.1055/a-1790-3230
account
Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis
Catalytic Kinetic Resolution and Desymmetrization of Amines
We gratefully acknowledge the National Natural Science Foundation of China (NSFC, Grant No. 22171186) and ShanghaiTech University startup funding for financial support.
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 catalysisPublication History
Received: 18 January 2022
Accepted after revision: 07 March 2022
Accepted Manuscript online:
07 March 2022
Article published online:
13 April 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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For selected examples of DKR of azlactones, see:
For selected examples of DKR of α-amino ketones, see:
For recent reviews on asymmetric reactions of aziridines, see: