{"title":"Asymmetric synthesis of axially chiral N,N′-carbazolepyrrole via copper-catalyzed Friedel–Crafts reaction†","authors":"Xin-Ru Wang and Yingying Zhang","doi":"10.1039/D5NJ00200A","DOIUrl":null,"url":null,"abstract":"<p >N–N atropisomers are commonly found in natural products and pharmaceuticals. Herein, we report a copper-bisoxazoline-catalyzed Friedel–Crafts reaction that enables the first enantioselective synthesis of <em>N,N</em>′-carbazole-pyrrole rings. This method demonstrates practical advantages with mild reaction conditions, an atom-economic process, high enantioselectivity and very broad substrate scope. Additionally, its scalability and versatility are showcased through gram-scale synthesis and diverse transformation applications.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":" 10","pages":" 3849-3854"},"PeriodicalIF":2.7000,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/nj/d5nj00200a","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Asymmetric synthesis of axially chiral N,N′-carbazolepyrrole via copper-catalyzed Friedel–Crafts reaction†
N–N atropisomers are commonly found in natural products and pharmaceuticals. Herein, we report a copper-bisoxazoline-catalyzed Friedel–Crafts reaction that enables the first enantioselective synthesis of N,N′-carbazole-pyrrole rings. This method demonstrates practical advantages with mild reaction conditions, an atom-economic process, high enantioselectivity and very broad substrate scope. Additionally, its scalability and versatility are showcased through gram-scale synthesis and diverse transformation applications.