{"title":"Ni-Catalyzed Stereodivergent Synthesis of N-Glycosides.","authors":"Jinhong Chen, Ruben Martin","doi":"10.1002/chem.202403822","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we describe a stereoselective Ni-catalyzed N-glycosylation of glycals. The reaction is enabled by addition of an in situ generated nickel hydride across an olefin prior to C-N bond-formation. Stereodivergence can be accomplished on kinetic or thermodynamic grounds, thus giving access to either α- or β-N-glycosides with equal ease. The protocol is distinguished by its operational simplicity, generality and exquisite selectivity, thus offering a new gateway to expedite the synthesis of N-glycosides.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202403822"},"PeriodicalIF":3.9000,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/chem.202403822","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we describe a stereoselective Ni-catalyzed N-glycosylation of glycals. The reaction is enabled by addition of an in situ generated nickel hydride across an olefin prior to C-N bond-formation. Stereodivergence can be accomplished on kinetic or thermodynamic grounds, thus giving access to either α- or β-N-glycosides with equal ease. The protocol is distinguished by its operational simplicity, generality and exquisite selectivity, thus offering a new gateway to expedite the synthesis of N-glycosides.
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