Cobalt(II)-Catalyzed C(sp3)-C(sp3) Coupling for the Direct Stereoselective Synthesis of 2-Deoxy-C-Glycosides from Glycals

被引：28
|
作者：
Zeng, Mingjie [1 ,2 ]
Yu, Changyue [2 ]
Wang, Yibing [2 ]
Wang, Jingjing [2 ]
Wang, Jiang [2 ,3 ]
Liu, Hong [1 ,2 ]
机构：
[1] China Pharmaceut Univ, 639 Longmian Ave, Nanjing 211198, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Chong Zhi Rd, Shanghai 201203, Peoples R China
[3] Lingang Lab, Shanghai 200031, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 22期
基金：
中国国家自然科学基金;
关键词：
Cobalt Catalysis; C(sp(3))-C(sp(3)) Coupling; beta-Configuration; 2-Deoxy-C-Glycosides; Radical Reactions; C-GLYCOSIDES; STRATEGY;
D O I：
10.1002/anie.202300424
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report a ligand-controlled Co-II-catalyzed C(sp(3))-C(sp(3)) coupling hydroalkylation for direct and beta-selective synthesis of 2-deoxy-C-glycosides from glycals. This reaction proceeds by a radical pathway for alkyl halide activation and is beta-selective through ligand control. This approach may inspire the development of further stereoselective coupling reactions with potential application in the field of carbohydrates.
引用
收藏
页数：6
相关论文
共 50 条
  • [41] Phosphorus and sulfur- ylide mediated C(sp3)-C(sp3)-coupling reactions
    Hock, Katharina
    Tran, Uyen
    Mertens, Lucas
    Gordon, Christopher
    Ho, Junming
    Thanh Nguyen
    Koenigs, Rene
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [42] C(sp3)-H/C(sp3)-H Dehydrogenative Radical Coupling of Glycine Derivatives
    Wang, Jiayuan
    Ye, Youwan
    Sang, Tongzhi
    Zhou, Chenxing
    Bao, Xiazhen
    Yuan, Yong
    Huo, Congde
    ORGANIC LETTERS, 2022, 24 (41) : 7577 - 7582
  • [43] C(sp3)-F, C(sp2)-F and C(sp3)-H bond activation at silicon(II) centers
    Swamy, V. S. V. S. N.
    Parvin, Nasrina
    Raj, K. Vipin
    Vanka, Kumar
    Sen, Sakya S.
    CHEMICAL COMMUNICATIONS, 2017, 53 (71) : 9850 - 9853
  • [44] Rhodium(I)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage
    Guo, Rui
    Zheng, Xinxin
    Zhang, Dayong
    Zhang, Guozhu
    CHEMICAL SCIENCE, 2017, 8 (04) : 3002 - 3006
  • [45] Palladium-Catalyzed Annulations via Sequential C-H Activations of C(sp2)-H/C(sp3)-H or C(sp3)-H/C(sp3)-H Bonds
    Wei, Wan-Xu
    Czajkowski, Mateusz
    Kuang, Yangjin
    Nguyen, Tu-Anh V.
    Qin, Bo
    Tomanik, Martin
    ACS CATALYSIS, 2024, 14 (09) : 6535 - 6546
  • [46] Asymmetric Amination of Unstrained C(sp3)-C(sp3) Bonds
    Liu, Yang
    Chen, Ye-Wei
    Yang, Yuan-Xiang
    Hartwig, John F.
    He, Zhi-Tao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (43) : 29857 - 29864
  • [47] Asymmetric allylic C(sp3)-C(sp3) bond functionalization
    He, Zhi-Tao
    NATURE SYNTHESIS, 2024, 3 (08): : 941 - 942
  • [48] Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners
    Li, Minyan
    Berritt, Simon
    Matuszewski, Lucas
    Deng, Guogang
    Pascual-Escudero, Ana
    Panetti, Grace B.
    Poznik, Michal
    Yang, Xiaodong
    Chruma, Jason J.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16327 - 16333
  • [49] Oxidative radical cascade cyclization involving C(sp3)-C(sp3), C(sp3)-C(sp2) and C(sp2)-N bonds formation: direct construction of cyano and methyl substituted polyheterocycles
    Shang, Jia-Qi
    Wang, Shi-Sheng
    Fu, Hong
    Li, Yi
    Yang, Tao
    Li, Ya-Min
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (12): : 1945 - 1949
  • [50] Intramolecular PdII-catalyzed dehydrogenative C(sp3)-C(sp2) coupling: an alternative to Pd0-catalyzed C(sp3)-H arylation from aryl halides?
    Pierre, Cathleen
    Baudoin, Olivier
    TETRAHEDRON, 2013, 69 (22) : 4473 - 4478
12345