{"title":"Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions","authors":"Jeyakumar Kandasamy, Adesh Kumar Singh, Rapelly Venkatesh","doi":"10.1055/a-2179-8669","DOIUrl":null,"url":null,"abstract":"Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"45 1","pages":"0"},"PeriodicalIF":2.2000,"publicationDate":"2023-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis-Stuttgart","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2179-8669","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.
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SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.
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