Direct Construction of C-Alkyl Glycosides from Non-Activated Olefins via Nickel-Catalyzed C(sp3)―C(sp3) Coupling Reaction
文献类型：期刊论文
| 作者 | Yu, Changyue1,2; Xu, Yinghuan1,2; Zeng, Mingjie3; Wang, Jingjing1,2; Dai, Wenhao1,2; Wang, Jiang4; Liu, Hong1,2,3
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| 刊名 | ADVANCED SCIENCE
 |
| 出版日期 | 2024-01-18 |
| 页码 | 8 |
| 关键词 | C-alkyl glycosides C(sp3)C(sp3) coupling non-activated olefins nickel catalysis |
| DOI | 10.1002/advs.202307226 |
| 通讯作者 | Wang, Jiang(jwang@lglab.ac.cn) ; Liu, Hong(hliu@simm.ac.cn) |
| 英文摘要 | Among C-glycosides, C-alkyl glycosides are significant building blocks for natural products and glycopeptides. However, research on efficient construction methods for C-alkyl glycosides remains relatively limited. Compared with Michael acceptors, non-activated olefins are more challenging substrates and have rarely been employed in the construction of C-glycosides. Here, a highly efficient and convenient approach for the synthesis of C-alkyl glycosides through a nickel-catalyzed C(sp(3))-C(sp(3)) coupling reaction is presented. A distinctive feature of this method is its utilization of non-activated olefins as the anomeric radical acceptors for hydroalkylation, allowing for the direct formation of C-glycoside bonds in a single step. Furthermore, this method demonstrates excellent compatibility with a broad scope of highly reactive functional groups. Mechanistic investigations suggest that the reaction proceeds via a free radical pathway, leading predominantly to the formation of products with alpha-configuration. Overall, this innovative methodology offers a versatile and practical approach for the synthesis of C-alkyl glycosides, offering new avenues for the production of intricate glycosides with potential applications in drug discovery and chemical biology. |
| WOS关键词 | H GLYCOSYLATION ; ANALOGS |
| 资助项目 | National Key R&D Program of China ; National Natural Science Foundation of China[82130105] ; National Natural Science Foundation of China[22337003] ; National Natural Science Foundation of China[82121005] ; National Natural Science Foundation of China[22177124] ; National Natural Science Foundation of China[82322063] ; National Natural Science Foundation of China[22107107] ; National Natural Science Foundation of China[LG-GG-202204-02] ; [2022YFA1302900] |
| WOS研究方向 | Chemistry ; Science & Technology - Other Topics ; Materials Science |
| 语种 | 英语 |
| WOS记录号 | WOS:001144575900001 |
| 出版者 | WILEY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/308684]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Wang, Jiang; Liu, Hong |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Univ Chinese Acad Sci, Sch Pharm, Beijing 100049, Peoples R China 3.China Pharmaceut Univ, Sch Pharm, Nanjing 211198, Peoples R China 4.Lingang Lab, Shanghai 200031, Peoples R China |
| 推荐引用方式 GB/T 7714 | Yu, Changyue,Xu, Yinghuan,Zeng, Mingjie,et al. Direct Construction of C-Alkyl Glycosides from Non-Activated Olefins via Nickel-Catalyzed C(sp3)―C(sp3) Coupling Reaction[J]. ADVANCED SCIENCE,2024:8. |
| APA | Yu, Changyue.,Xu, Yinghuan.,Zeng, Mingjie.,Wang, Jingjing.,Dai, Wenhao.,...&Liu, Hong.(2024).Direct Construction of C-Alkyl Glycosides from Non-Activated Olefins via Nickel-Catalyzed C(sp3)―C(sp3) Coupling Reaction.ADVANCED SCIENCE,8. |
| MLA | Yu, Changyue,et al."Direct Construction of C-Alkyl Glycosides from Non-Activated Olefins via Nickel-Catalyzed C(sp3)―C(sp3) Coupling Reaction".ADVANCED SCIENCE (2024):8. |
入库方式： OAI收割
来源：上海药物研究所
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