Title | Synthesis of Chiral Primary Amines via Enantioselective Reductive Amination: From Academia to Industry |
Author | |
Corresponding Author | Zhang, Xumu; Yin, Qin |
Publication Years | 2023
|
DOI | |
Source Title | |
ISSN | 0039-7881
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EISSN | 1437-210X
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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]
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WOS Research Area | Chemistry
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WOS Subject | Chemistry, Organic
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WOS Accession No | WOS:000919253100003
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Publisher | |
ESI Research Field | CHEMISTRY
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Data Source | Web of Science
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Citation statistics |
Cited Times [WOS]:4
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Document Type | Journal Article |
Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/475055 |
Department | Department 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 Affilication | Department of Chemistry |
Corresponding Author Affilication | Department of Chemistry |
First Author's First Affilication | Department 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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