Jia-Le Yan, Zhi-Lin Liu, Kai Chen, Hao-Yue Xiang, Hua Yang
{"title":"EDA-Enabled Three-Component Polarity-Crossover Cyclization: Modular Installation of Fully Substituted γ-Lactams.","authors":"Jia-Le Yan, Zhi-Lin Liu, Kai Chen, Hao-Yue Xiang, Hua Yang","doi":"10.1021/acs.orglett.4c03745","DOIUrl":null,"url":null,"abstract":"<p><p>A photoinduced three-component radical addition-aminalization cascade was accomplished, enabling rapid assembly of a wide range of densely functionalized γ-lactams. Key to this transformation is the electron-donor-acceptor (EDA) generation of enamine and in situ trapping of an iminium intermediate with bromodifluoroacetamide. This rationally designed protocol fully takes advantage of the polarity crossover (enamine-iminium) in the process, providing the modular assembly of previously inaccessible scaffolds. The reaction proceeds under mild reaction conditions with excellent regio- and diastereoselectivity, which is amenable to structurally varied substrates and pharmaceuticals.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03745","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/28 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A photoinduced three-component radical addition-aminalization cascade was accomplished, enabling rapid assembly of a wide range of densely functionalized γ-lactams. Key to this transformation is the electron-donor-acceptor (EDA) generation of enamine and in situ trapping of an iminium intermediate with bromodifluoroacetamide. This rationally designed protocol fully takes advantage of the polarity crossover (enamine-iminium) in the process, providing the modular assembly of previously inaccessible scaffolds. The reaction proceeds under mild reaction conditions with excellent regio- and diastereoselectivity, which is amenable to structurally varied substrates and pharmaceuticals.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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