{"title":"Sc(OTf)3-Catalyzed Diastereoselective Hydroxyheteroarylation of C–C σ-Bonds of Bicyclo[1.1.0]butanes with Azaheterocyclic N-Oxides","authors":"Jiang Wang, Jiajia Liu, Chenwei Li, Jing Liu, Kailiang Ding, Jinzhong Yao, Maozhong Miao","doi":"10.1021/acs.orglett.5c00802","DOIUrl":null,"url":null,"abstract":"A mild and atom-economical reaction for the Sc(OTf)<sub>3</sub>-catalyzed 1,3-hydroxyheteroarylation of bicyclo[1.1.0]butanes (BCBs) with azaaryl <i>N</i>-oxides via an unprecedented [4π+2σ] cycloaddition/ring-opening process is described. This transformation provides a novel strategy for the highly regio- and diastereoselective preparation of azaheterocycle-tethered 1,1,3,3-tetrasubstituted cyclobutane derivatives and offers a broad substrate scope and high yields.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-22","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.5c00802","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
A mild and atom-economical reaction for the Sc(OTf)3-catalyzed 1,3-hydroxyheteroarylation of bicyclo[1.1.0]butanes (BCBs) with azaaryl N-oxides via an unprecedented [4π+2σ] cycloaddition/ring-opening process is described. This transformation provides a novel strategy for the highly regio- and diastereoselective preparation of azaheterocycle-tethered 1,1,3,3-tetrasubstituted cyclobutane derivatives and offers a broad substrate scope and high yields.
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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