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Regio- and Diastereoselective Construction of Multisubstituted C-Vinyl Glycosides via Nickel-Catalyzed Three-Component Reaction of Alkynes

文献类型：期刊论文

作者Wang, Jinlin2,3; Yu, Changyue2; Zhong, Qiuyu2,4; Zeng, Mingjie2,4; He, Xiaofei2,4; Li, Chunpu1,2,3; Wang, Jiang5; Dai, Wenhao1,2,3; Liu, Hong1,2,3,4
刊名ACS CATALYSIS
出版日期2025-10-03
卷号15期号:19页码:16762-16770
关键词C-vinyl glycosides nickelcatalysis three-componentreaction radicals alkynes
ISSN号2155-5435
DOI10.1021/acscatal.5c03229
英文摘要C-vinyl glycosides are important carbohydrates with various biological activities and promising applications. However, the efficient synthesis of C-vinyl glycosides remains challenging, typically relying on two-component couplings of glycosyl donors with olefins or alkynes. These methods often involve air-sensitive organometallic reagents, directing groups, or activating group preactivation. Notably, the construction of multisubstituted C-vinyl glycosides directly from alkynes remains largely underexplored in synthetic carbohydrate chemistry. Here, a convenient and efficient method for the regio- and diastereoselective synthesis of multisubstituted C-vinyl glycosides via a nickel-catalyzed three-component reaction involving terminal alkynes, boronic acids, and glycosyl bromides in one pot is presented. This reaction proceeds by a radical pathway and demonstrates excellent regio- and diastereoselectivity, as evidenced by the alpha-selective, trans-addition products and the addition of the glycosyl moiety installed at the terminal position of the alkyne. This method utilizes commercially available starting materials without the need for additional preactivation, features a straightforward operational procedure, and demonstrates a broad substrate scope and functional group tolerance. Furthermore, this method is suitable for the late-stage glycosylation modification of complex natural products. Overall, this approach provides a widely applicable method to synthesize multisubstituted C-vinyl glycosides using simple and readily available three-component starting materials in one pot.
WOS关键词ARYL
资助项目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[82341091] ; National Natural Science Foundation of China[22107107] ; National Natural Science Foundation of China[U22A20379] ; National Natural Science Foundation of China[2023292] ; Youth Innovation Promotion Association CAS
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001575450300001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/321522]  
专题国家级研究中心_原创新药研究全国重点实验室
通讯作者Dai, Wenhao; Liu, Hong
作者单位1.UCAS, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
3.Univ Chinese Acad Sci, Sch Pharm, Beijing 100049, Peoples R China
4.China Pharmaceut Univ, Nanjing 211198, Peoples R China
5.Lingang Lab, Shanghai 200031, Peoples R China
推荐引用方式
GB/T 7714		 Wang, Jinlin,Yu, Changyue,Zhong, Qiuyu,et al. Regio- and Diastereoselective Construction of Multisubstituted C-Vinyl Glycosides via Nickel-Catalyzed Three-Component Reaction of Alkynes[J]. ACS CATALYSIS,2025,15(19):16762-16770.
APA Wang, Jinlin.,Yu, Changyue.,Zhong, Qiuyu.,Zeng, Mingjie.,He, Xiaofei.,...&Liu, Hong.(2025).Regio- and Diastereoselective Construction of Multisubstituted C-Vinyl Glycosides via Nickel-Catalyzed Three-Component Reaction of Alkynes.ACS CATALYSIS,15(19),16762-16770.
MLA Wang, Jinlin,et al."Regio- and Diastereoselective Construction of Multisubstituted C-Vinyl Glycosides via Nickel-Catalyzed Three-Component Reaction of Alkynes".ACS CATALYSIS 15.19(2025):16762-16770.

入库方式： OAI收割

来源：上海药物研究所

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