中文版 | English
Title

Synthesis of Chiral Primary Amines via Enantioselective Reductive Amination: From Academia to Industry

Author
Corresponding AuthorZhang, Xumu; Yin, Qin
Publication Years
2023
DOI
Source Title
ISSN
0039-7881
EISSN
1437-210X
Abstract
Chiral primary amines widely exist in drugs and are exceptionally important subunits or synthons in the syntheses of chiral secondary and tertiary amines of medicinal interest. Metal-catalyzed enantioselective reductive amination (ERA) of ketones with ammonium salts or ammonia provides a direct method for their synthesis. Although very useful, progress in this field has been very slow and important advances have only been achieved in the last few years. Several major challenges exist in this reaction, including (1) the reversible formation of unstable NH-imine intermediates; (2) the strong coordination property of N containing reagents toward metal species; and (3) the lack of efficient catalytic systems that enable high enantiocontrol. Generally, the efficiency and enantiocontrol of this reaction is dependent on the substrate type, for instance, the use of alpha-keto esters/amides or aryl alkyl ketones is well established and they have even been used in the industrial production of chiral amine drugs. However, highly enantioselective control in dialkyl ketones, cyclic ketones, and alpha-keto acids remains unsolved. Herein, the historical development of ERA reactions with ammonium salts or ammonia gas is summarized, and novel synthetic applications toward useful synthons or drugs are presented. In addition, the factors restricting the growth of this method are also discussed.1 Introduction2 Enantioselective Reductive Amination via Hydrogenation2.1 Enantioselective Reductive Amination of beta-Keto Esters/Amides2.2 Enantioselective Reductive Amination of Simple Ketones2.3 Enantioselective Reductive Amination of alpha-Functionalized Ketones2.4 Enantioselective Reductive Amination/Cyclization Cascade Reactions2.5 Others3 Enantioselective Reductive Amination via Transfer Hydrogenation4 Synthetic Applications5 Conclusions and Outlook
Keywords
URL[Source Record]
Indexed By
Language
English
SUSTech Authorship
First ; Corresponding
Funding Project
National Natural Science Foundation of China["22071097","21991113"] ; Shenzhen Science and Technology Innovation Program["JCYJ20190809142013478","JCYJ20220818100804010"] ; Guangdong Basic and Applied Basic Research Foundation[2021B1515020062]
WOS Research Area
Chemistry
WOS Subject
Chemistry, Organic
WOS Accession No
WOS:000919253100003
Publisher
ESI Research Field
CHEMISTRY
Data Source
Web of Science
Citation statistics
Cited Times [WOS]:4
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/475055
DepartmentDepartment of Chemistry
Affiliation
1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
2.Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Peoples R China
First Author AffilicationDepartment of Chemistry
Corresponding Author AffilicationDepartment of Chemistry
First Author's First AffilicationDepartment of Chemistry
Recommended Citation
GB/T 7714
Shi, Yongjie,Rong, Nianxin,Zhang, Xumu,et al. Synthesis of Chiral Primary Amines via Enantioselective Reductive Amination: From Academia to Industry[J]. SYNTHESIS-STUTTGART,2023.
APA
Shi, Yongjie,Rong, Nianxin,Zhang, Xumu,&Yin, Qin.(2023).Synthesis of Chiral Primary Amines via Enantioselective Reductive Amination: From Academia to Industry.SYNTHESIS-STUTTGART.
MLA
Shi, Yongjie,et al."Synthesis of Chiral Primary Amines via Enantioselective Reductive Amination: From Academia to Industry".SYNTHESIS-STUTTGART (2023).
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