Mukund P. Sibi, Tara R. Rheault , Hideto Miyabe , Kalyani Patil, Craig P. Jasperse
{"title":"Highly diastereoselective radical addition–cyclization strategy: facile synthesis of substituted furans","authors":"Mukund P. Sibi, Tara R. Rheault , Hideto Miyabe , Kalyani Patil, Craig P. Jasperse","doi":"10.1016/S1387-1609(01)01279-8","DOIUrl":null,"url":null,"abstract":"<div><p>A novel strategy is described in which an intermolecular carbon-centered radical addition to a β-oxygenated acceptor followed by intramolecular cyclization leads to the formation of 2,3,4- and 2,3,4,5-substituted furan rings. Excellent levels of 2,4-<em>trans</em> selectivity are observed in accordance with the Beckwith–Houk model for selectivity in 5-<em>exo</em> radical cyclizations.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 7","pages":"Pages 581-584"},"PeriodicalIF":0.0000,"publicationDate":"2001-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01279-8","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1387160901012798","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A novel strategy is described in which an intermolecular carbon-centered radical addition to a β-oxygenated acceptor followed by intramolecular cyclization leads to the formation of 2,3,4- and 2,3,4,5-substituted furan rings. Excellent levels of 2,4-trans selectivity are observed in accordance with the Beckwith–Houk model for selectivity in 5-exo radical cyclizations.
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