Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams

Zheng, Jing-Jing1,2; Liu, Wei-Long1,2; Gu, Qiang-Shuai3; Li, Zhong-Liang3; Chen, Ji-Jun1,2; Liu, Xin-Yuan1,2

2023-12-25

10.1021/prechem.3c00084

Precision Chemistry   影响因子和分区

2771-9316

2771-9316

A copper-catalyzed enantioconvergent radical C(sp(3))-N cross-coupling of racemic tertiary alpha-bromo-beta-lactams with aromatic amines is developed under mild thermal reaction conditions. The use of a sterically demanded oxazoline-derived sulfonamide N,N,N-ligand is crucial for the reaction initiation and effective enantio-discrimination of the azetidinone-derived cyclic alkyl radicals. The strategy provides an attractive approach to access chiral alpha-amino-beta-lactams, an important structural motif in many biologically active molecules. Preliminary mechanistic studies support the formation of azetidinone-derived alkyl radicals from the L*Cu(I)-amido complex and alpha-bromo-beta-lactams.

copper asymmetric radical reactions cross-coupling aromatic amines chiral alpha-amino-beta-lactams

ESCI

英语

第一 ; 共同第一 ; 通讯

National Key R&D Program of China["2021YFF0701604","2021YFF0701704"] ; National Natural Science Foundation of China["22025103","92256301","21831002","22271133"] ; Shenzhen Key Laboratory of Cross-Coupling Reactions[ZDSYS20220328104200001] ; Shenzhen Science and Technology Program["KQTD20210811090112004","JCYJ20200109141001789","JCYJ20220818100600001","JCYJ202205300115409020"]

Chemistry

Chemistry, Multidisciplinary

WOS:001280742700001

American Chemical Society (ACS)

人工提交

正式出版

1.Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology, Shenzhen 518055, China
2.Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
3.Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China

Zheng, Jing-Jing,Liu, Wei-Long,Gu, Qiang-Shuai,等. Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams[J]. Precision Chemistry,2023,1(10):576-582.

Zheng, Jing-Jing,Liu, Wei-Long,Gu, Qiang-Shuai,Li, Zhong-Liang,Chen, Ji-Jun,&Liu, Xin-Yuan.(2023).Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams.Precision Chemistry,1(10),576-582.

Zheng, Jing-Jing,et al."Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams".Precision Chemistry 1.10(2023):576-582.