{"title":"Synthesis of aryl enopyranones directly from glycals and aromatic halides to access 2-deoxy-β-C-aryl glycosides†","authors":"","doi":"10.1039/d4ob01172d","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient synthesis of aryl enopyranones <em>via</em> an oxidative Heck-type coupling reaction between ether protected <span>d</span>/<span>l</span>-glycals and different aryl halides is developed. This one-step method attaches an aryl group at the C-1 position keeping the C-1/C-2 double bond intact <em>via</em> the Saegusa–Ito type oxidation, thus facilitating the synthesis of medicinally important 2-deoxy-β-aryl-C-glycosides after Pd/C reduction.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024006888","RegionNum":3,"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
An efficient synthesis of aryl enopyranones via an oxidative Heck-type coupling reaction between ether protected d/l-glycals and different aryl halides is developed. This one-step method attaches an aryl group at the C-1 position keeping the C-1/C-2 double bond intact via the Saegusa–Ito type oxidation, thus facilitating the synthesis of medicinally important 2-deoxy-β-aryl-C-glycosides after Pd/C reduction.