{"title":"Precise Modulation of BCB Reactive Sites via Lewis/Brønsted Acid Switching for the Synthesis of Spirocycles and Bridged Frameworks.","authors":"Ming-Ming Li,Teng-Fei Xiao,Yi-Xiang Geng,Guo-Qiang Xu,Peng-Fei Xu","doi":"10.1021/acs.orglett.5c02160","DOIUrl":null,"url":null,"abstract":"Bicyclo[1.1.0]butanes (BCBs), which possess multiple switchable reactive sites, serve as the most direct modular scaffolds for constructing benzene ring bioisosteres. Herein, we describe the precise modulation of BCB reactive sites through Lewis/Brønsted acid switching to enable the synthesis of challenging spirocycles and bridged frameworks. The divergent reaction outcomes, arising from the precise control of catalysts over the switchable reactive sites of BCBs, are achieved without any substrate modification.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"3 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-07-09","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.5c02160","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
Bicyclo[1.1.0]butanes (BCBs), which possess multiple switchable reactive sites, serve as the most direct modular scaffolds for constructing benzene ring bioisosteres. Herein, we describe the precise modulation of BCB reactive sites through Lewis/Brønsted acid switching to enable the synthesis of challenging spirocycles and bridged frameworks. The divergent reaction outcomes, arising from the precise control of catalysts over the switchable reactive sites of BCBs, are achieved without any substrate modification.
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.