{"title":"Gold(I)-Catalyzed Asymmetric Heterocyclization/(5 + 3) Cycloaddition of Yne-enones with Imidazolidines: Access to Cycloocta[c]furan Frameworks.","authors":"Yuncheng Liu,Xiaoai Liu,Songyi Gao,Junyang Liu,Ming Lang,Shiyong Peng","doi":"10.1021/acs.orglett.5c01267","DOIUrl":null,"url":null,"abstract":"Herein, we report a gold(I)-catalyzed heterocyclization/(5 + 3) cycloaddition cascade of yne-enones with imidazolidines, providing a modular, atom-economical and efficient strategy for the synthesis of cycloocta[c]furans in moderate to excellent yields. This method features readily available substrates, simple operation, mild reaction conditions, and broad substrate scope. More importantly, the asymmetric version is also achieved by employing (R)-C2-TunePhos ligand (L7), leading to optically active cycloocta[c]furans with up to 98:2 er.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"9 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-12","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.5c01267","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report a gold(I)-catalyzed heterocyclization/(5 + 3) cycloaddition cascade of yne-enones with imidazolidines, providing a modular, atom-economical and efficient strategy for the synthesis of cycloocta[c]furans in moderate to excellent yields. This method features readily available substrates, simple operation, mild reaction conditions, and broad substrate scope. More importantly, the asymmetric version is also achieved by employing (R)-C2-TunePhos ligand (L7), leading to optically active cycloocta[c]furans with up to 98:2 er.
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.