{"title":"镍催化立体发散合成n -糖苷。","authors":"Jinhong Chen, Ruben Martin","doi":"10.1002/chem.202403822","DOIUrl":null,"url":null,"abstract":"<p>Herein, we describe a stereoselective Ni-catalyzed <i>N</i>-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-<i>N</i>-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 <i>N</i>-glycosides.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":"31 7","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ni-Catalyzed Stereodivergent Synthesis of N-Glycosides\",\"authors\":\"Jinhong Chen, Ruben Martin\",\"doi\":\"10.1002/chem.202403822\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Herein, we describe a stereoselective Ni-catalyzed <i>N</i>-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-<i>N</i>-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 <i>N</i>-glycosides.</p>\",\"PeriodicalId\":144,\"journal\":{\"name\":\"Chemistry - A European Journal\",\"volume\":\"31 7\",\"pages\":\"\"},\"PeriodicalIF\":3.6000,\"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://chemistry-europe.onlinelibrary.wiley.com/doi/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}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://chemistry-europe.onlinelibrary.wiley.com/doi/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
摘要
在这里，我们描述了一个立体选择性镍催化的n -糖基化的糖醛。该反应是通过在形成C-N键之前在烯烃上添加原位生成的氢化镍来实现的。立体发散可以在动力学或热力学的基础上完成，从而可以同样容易地获得α-或β- n -糖苷。该方案具有操作简单、通用性强、选择性好等特点，为加快n -糖苷的合成提供了新的途径。
Ni-Catalyzed Stereodivergent Synthesis of N-Glycosides
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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