Bowen Li, Valero G Alfonso, Alessio Puggioli, Albert Solé-Daura, Feliu Maseras, Marcos G Suero
{"title":"Rh-Catalyzed Atroposelective Single-Carbon Insertion.","authors":"Bowen Li, Valero G Alfonso, Alessio Puggioli, Albert Solé-Daura, Feliu Maseras, Marcos G Suero","doi":"10.1021/jacs.5c06139","DOIUrl":null,"url":null,"abstract":"<p><p>Single-carbon insertion processes have gained considerable momentum over the past few years. Although innovative methods have emerged for converting indole or indene into quinoline or naphthalene cores, the enantioselective version of such ring-expansions to create (hetero)biaryl atropisomers has not been developed. Herein, we report the first enantioselective single-carbon insertion that converts 3-aryl indoles to atropochiral quinolines. Key in the process was the generation of a chiral Rh-carbynoid that mediated in the creation of the stereogenic C(<i>sp</i><sup>2</sup>)-C(<i>sp</i><sup>2</sup>) axis.</p>","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":" ","pages":""},"PeriodicalIF":14.4000,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.5c06139","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Single-carbon insertion processes have gained considerable momentum over the past few years. Although innovative methods have emerged for converting indole or indene into quinoline or naphthalene cores, the enantioselective version of such ring-expansions to create (hetero)biaryl atropisomers has not been developed. Herein, we report the first enantioselective single-carbon insertion that converts 3-aryl indoles to atropochiral quinolines. Key in the process was the generation of a chiral Rh-carbynoid that mediated in the creation of the stereogenic C(sp2)-C(sp2) axis.
期刊介绍:
The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.