{"title":"Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade","authors":"Jian-Yu Pang, Li-Min Feng, Wen-Feng Zhang, De-Yong Liu, Jing Wang, Ruo-Han Wei, Xiang-Guo Hu","doi":"10.1021/acs.orglett.4c04510","DOIUrl":null,"url":null,"abstract":"We have developed a glycosyl radical-based synthesis of <i>C</i>-alkyl glycosides through a deoxygenative Giese addition–reduction–cyclization cascade, in which readily available 1-hydroxy carbohydrates serve as precursors for glycosyl radicals and aryl alkenes function as radical acceptors. This reaction not only provides an effective method for accessing a previously underexplored class of functionalized cyclopropanes but also enhances the application of Giese addition in the synthesis of <i>C</i>-alkyl glycosides by derivatizing the radical intermediate generated through polar cyclization to yield a cyclopropane.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"77 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-23","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.4c04510","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
We have developed a glycosyl radical-based synthesis of C-alkyl glycosides through a deoxygenative Giese addition–reduction–cyclization cascade, in which readily available 1-hydroxy carbohydrates serve as precursors for glycosyl radicals and aryl alkenes function as radical acceptors. This reaction not only provides an effective method for accessing a previously underexplored class of functionalized cyclopropanes but also enhances the application of Giese addition in the synthesis of C-alkyl glycosides by derivatizing the radical intermediate generated through polar cyclization to yield a cyclopropane.
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.