{"title":"Synthesis of 2,5-Dithia-bicyclo[4.1.1]octanes by Silver-Catalyzed Formal (4+3) Cycloadditions of Bicyclobutanes with Benzodithioloimines","authors":"Xuechen Zhou, Jianyang Dong, Huijuan Liao, Qin Jiang, Bowen Zhang, Ting Li, Fang Lei, Huaming Sun, Dong Xue","doi":"10.1021/acs.orglett.5c00585","DOIUrl":null,"url":null,"abstract":"Cycloadditions of bicyclobutanes with two- or three-atom reaction partners have been widely exploited to access bicyclo[2.1.1]hexanes and bicyclo[3.1.1]heptanes. However, their application to the synthesis of bicyclo[4.1.1]octane derivatives has remained elusive. Herein, we report silver-catalyzed formal (4+3) cycloadditions between simple bicyclobutanes and benzodithioloimines, establishing a new method for synthesizing previously inaccessible 2,5-dithia-bicyclo[4.1.1]octanes, which have two sulfur atoms in their bicyclo[4.1.1]octane frameworks. This mild method tolerates bicyclobutane substrates with a wide range of substituents. The synthetic utility of this method was demonstrated via various synthetic transformations of the products to yield valuable sulfur-containing bridged bicyclic scaffolds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-03-30","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.5c00585","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
Cycloadditions of bicyclobutanes with two- or three-atom reaction partners have been widely exploited to access bicyclo[2.1.1]hexanes and bicyclo[3.1.1]heptanes. However, their application to the synthesis of bicyclo[4.1.1]octane derivatives has remained elusive. Herein, we report silver-catalyzed formal (4+3) cycloadditions between simple bicyclobutanes and benzodithioloimines, establishing a new method for synthesizing previously inaccessible 2,5-dithia-bicyclo[4.1.1]octanes, which have two sulfur atoms in their bicyclo[4.1.1]octane frameworks. This mild method tolerates bicyclobutane substrates with a wide range of substituents. The synthetic utility of this method was demonstrated via various synthetic transformations of the products to yield valuable sulfur-containing bridged bicyclic scaffolds.
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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