{"title":"可见光促进Ir(III)催化1-溴糖立体选择性合成azauracil - c核苷。","authors":"Ramanand Das,Norein Sakander,Sanchari Kundu,Debaraj Mukherjee,Taraknath Kundu","doi":"10.1021/acs.orglett.5c01474","DOIUrl":null,"url":null,"abstract":"A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor and 6-azauracil as the nucleobase. The method exhibits high α-selectivity and excellent functional group tolerance. Spectroscopic evidence shows that the coupling reaction happens via initial reductive quenching of the Ir(III) catalyst under visible light. Density functional theory calculation reveals the reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making the process a valuable platform for C-nucleosides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"79 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar.\",\"authors\":\"Ramanand Das,Norein Sakander,Sanchari Kundu,Debaraj Mukherjee,Taraknath Kundu\",\"doi\":\"10.1021/acs.orglett.5c01474\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor and 6-azauracil as the nucleobase. The method exhibits high α-selectivity and excellent functional group tolerance. Spectroscopic evidence shows that the coupling reaction happens via initial reductive quenching of the Ir(III) catalyst under visible light. Density functional theory calculation reveals the reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making the process a valuable platform for C-nucleosides.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"79 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-05-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c01474\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01474","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Visible Light-Promoted Ir(III)-Catalyzed Stereoselective Synthesis of Azauracil-C-Nucleosides from 1-Bromosugar.
A visible light-promoted, mild, and efficient Ir(III)-catalyzed synthesis of C-nucleosides is reported, utilizing 1-bromosugar as the glycosyl radical precursor and 6-azauracil as the nucleobase. The method exhibits high α-selectivity and excellent functional group tolerance. Spectroscopic evidence shows that the coupling reaction happens via initial reductive quenching of the Ir(III) catalyst under visible light. Density functional theory calculation reveals the reason for complete α-selectivity. Finally, biologically active 6-aza pseudouridine analogues were synthesized, making the process a valuable platform for C-nucleosides.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.