{"title":"铜催化对映体自由基 C(sp3)-N 交叉偶联以获得手性 α-氨基-β-内酰胺","authors":"Jing-Jing Zheng, Wei-Long Liu, Qiang-Shuai Gu, Zhong-Liang Li, Ji-Jun Chen* and Xin-Yuan Liu*, ","doi":"10.1021/prechem.3c00084","DOIUrl":null,"url":null,"abstract":"<p >A copper-catalyzed enantioconvergent radical C(sp<sup>3</sup>)–N cross-coupling of racemic tertiary α-bromo-β-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 α-amino-β-lactams, an important structural motif in many biologically active molecules. Preliminary mechanistic studies support the formation of azetidinone-derived alkyl radicals from the <b>L*</b>Cu(I)-amido complex and α-bromo-β-lactams.</p>","PeriodicalId":29793,"journal":{"name":"Precision Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2023-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/prechem.3c00084","citationCount":"0","resultStr":"{\"title\":\"Copper-Catalyzed Enantioconvergent Radical C(sp3)–N Cross-Coupling to Access Chiral α-Amino-β-lactams\",\"authors\":\"Jing-Jing Zheng, Wei-Long Liu, Qiang-Shuai Gu, Zhong-Liang Li, Ji-Jun Chen* and Xin-Yuan Liu*, \",\"doi\":\"10.1021/prechem.3c00084\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A copper-catalyzed enantioconvergent radical C(sp<sup>3</sup>)–N cross-coupling of racemic tertiary α-bromo-β-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 α-amino-β-lactams, an important structural motif in many biologically active molecules. Preliminary mechanistic studies support the formation of azetidinone-derived alkyl radicals from the <b>L*</b>Cu(I)-amido complex and α-bromo-β-lactams.</p>\",\"PeriodicalId\":29793,\"journal\":{\"name\":\"Precision Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-10-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/epdf/10.1021/prechem.3c00084\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Precision Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/prechem.3c00084\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Precision Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/prechem.3c00084","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Copper-Catalyzed Enantioconvergent Radical C(sp3)–N Cross-Coupling to Access Chiral α-Amino-β-lactams
A copper-catalyzed enantioconvergent radical C(sp3)–N cross-coupling of racemic tertiary α-bromo-β-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 α-amino-β-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 α-bromo-β-lactams.
期刊介绍:
Chemical research focused on precision enables more controllable predictable and accurate outcomes which in turn drive innovation in measurement science sustainable materials information materials personalized medicines energy environmental science and countless other fields requiring chemical insights.Precision Chemistry provides a unique and highly focused publishing venue for fundamental applied and interdisciplinary research aiming to achieve precision calculation design synthesis manipulation measurement and manufacturing. It is committed to bringing together researchers from across the chemical sciences and the related scientific areas to showcase original research and critical reviews of exceptional quality significance and interest to the broad chemistry and scientific community.