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Zirconaaziridine-Mediated Ni-Catalyzed Diastereoselective C(sp2)-Glycosylation | |
2024-06-11 | |
发表期刊 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (IF:14.4[JCR-2023],14.8[5-Year]) |
ISSN | 0002-7863 |
EISSN | 1520-5126 |
卷号 | 146期号:24页码:16753-16763 |
发表状态 | 已发表 |
DOI | 10.1021/jacs.4c04587 |
摘要 | In the realm of organic synthesis, the catalytic and stereoselective formation of C-glycosidic bonds is a pivotal process, bridging carbohydrates with aglycones. However, the inherent chirality of the saccharide scaffold often has a substantial impact on the stereoinduction imposed by a chiral ligand. In this study, we have established an unprecedented zirconaaziridine-mediated asymmetric nickel catalysis, enabling the diastereoselective coupling of bench-stable glycosyl phosphates with a range of (hetero)aromatic and glycal iodides as feasible coupling electrophiles. Our developed method showcases a broad scope and a high tolerance for various functional groups. More importantly, precise stereocontrol toward both anomeric configurations of forming C(sp(2))-glycosides can be realized by simply utilizing the popular chiral bioxazoline (biOx) ligands in this reductive Ni catalysis. Regarding the operating mechanism, both experimental and computational studies support the occurrence of a redox transmetalation process, leading to the formation of a transient, bimetallic Ni-Zr species that acts as a potent and efficient single-electron reductant in the catalytic process. |
关键词 | Binary alloys Catalysis Scaffolds Stereoselectivity Zircaloy Aglycones Catalytic formation Chiral ligand Diastereoselective Glycosidic bond Glycosylations Inherent chiralities Nickel catalysis Organic synthesis Stereoselective formation |
URL | 查看原文 |
收录类别 | SCI ; EI |
语种 | 英语 |
资助项目 | ShanghaiTech University[2022YFA1504301] ; National Key R&D Program of China[ |
WOS研究方向 | Chemistry |
WOS类目 | Chemistry, Multidisciplinary |
WOS记录号 | WOS:001245114700001 |
出版者 | AMER CHEMICAL SOC |
EI入藏号 | 20242516275206 |
EI主题词 | Ligands |
EI分类号 | 405.1 Construction Equipment ; 531 Metallurgy and Metallography ; 801 Chemistry ; 801.4 Physical Chemistry ; 802.2 Chemical Reactions |
原始文献类型 | Journal article (JA) |
引用统计 | 正在获取...
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文献类型 | 期刊论文 |
条目标识符 | https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/395913 |
专题 | 物质科学与技术学院 物质科学与技术学院_硕士生 物质科学与技术学院_本科生 物质科学与技术学院_博士生 物质科学与技术学院_PI研究组_叶柏华组 |
通讯作者 | Hong, Xin; Ye, Baihua |
作者单位 | 1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China 2.Zhejiang Univ, Ctr Chem Frontier Technol, Dept Chem, State Key Lab Clean Energy Utilizat, Hangzhou 310027, Peoples R China 3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China 4.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China 5.Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 6.Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China |
第一作者单位 | 物质科学与技术学院 |
通讯作者单位 | 物质科学与技术学院 |
第一作者的第一单位 | 物质科学与技术学院 |
推荐引用方式 GB/T 7714 | Gan, Yu,Zhou, Jun-Feng,Li, Xuejiao,et al. Zirconaaziridine-Mediated Ni-Catalyzed Diastereoselective C(sp2)-Glycosylation[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024,146(24):16753-16763. |
APA | Gan, Yu.,Zhou, Jun-Feng.,Li, Xuejiao.,Liu, Ji-Ren.,Liu, Fang-Jie.,...&Ye, Baihua.(2024).Zirconaaziridine-Mediated Ni-Catalyzed Diastereoselective C(sp2)-Glycosylation.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,146(24),16753-16763. |
MLA | Gan, Yu,et al."Zirconaaziridine-Mediated Ni-Catalyzed Diastereoselective C(sp2)-Glycosylation".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146.24(2024):16753-16763. |
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