Cobalt(III)-Catalyzed Diastereo- and Enantioselective Three-Component C-H Functionalization

被引:45
|
作者
Herraiz, Ana G. [1 ]
Cramer, Nicolai [1 ]
机构
[1] Ecole Polytech Fed Lausanne EPFL, Lab Asymmetr Catalysis & Synth, Inst Chem Sci & Engn, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
asymmetric catalysis; cobalt; C-H functionalization; chiral cyclopentadienyl; multicomponent reaction; ASYMMETRIC FUNCTIONALIZATION; MULTICOMPONENT REACTIONS; BOND FUNCTIONALIZATION; ACTIVATION; CATALYSIS; LIGANDS; ALKENES; RH;
D O I
10.1021/acscatal.1c03153
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Catalytic enantioselective C-H functionalization has recently become a tool for the creation of stereogenic centers. The steep increase in molecular complexity of multicomponent reactions matches very well with asymmetric C-H functionalizations, but the realization of such processes remains a large challenge. We describe a diastereoselective and highly enantioselective three-component C-H functionalization catalyzed by an earth-abundant Co(III) complex equipped with a chiral cyclopentadienyl ligand (Cp-x). The transformation provides a rapid access to substituted beta-hydroxyketones using three readily accessible starting materials. The outlined reactivity of (CpCo)-Co-x(III) catalysis shows a higher and exploitable propensity for selective additions across carbonyls in contrast to the chemistry of Rh(III).
引用
收藏
页码:11938 / 11944
页数:7
相关论文
共 50 条
  • [41] Diastereo- and Enantioselective Synthesis of Organometallic Bis(helicene)s by a Combination of C-H Activation and Dynamic Isomerization
    Shen, Chengshuo
    Anger, Emmanuel
    Srebro, Monika
    Vanthuyne, Nicolas
    Toupet, Loic
    Roussel, Christian
    Autschbach, Jochen
    Reau, Regis
    Crassous, Jeanne
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) : 16722 - 16728
  • [42] Ruthenium-catalyzed three-component tandem remote C-H functionalization of naphthalenes: modular and concise synthesis of multifunctional naphthalenes
    Huang, Mao-Gui
    Fu, Yue-Liu-Ting
    Li, Jia-Wei
    Liu, Yue-Jin
    CHEMICAL SCIENCE, 2025, 16 (04) : 1957 - 1965
  • [43] Cobalt-Catalyzed Enantioselective C-H Annulation with Alkenes
    Yang, Dandan
    Zhang, Xian
    Wang, Xinghua
    Si, Xiao-Ju
    Wang, Jingtao
    Wei, Donghui
    Song, Mao-Ping
    Niu, Jun-Long
    ACS CATALYSIS, 2023, 13 (07): : 4250 - 4260
  • [44] Cobalt-Catalyzed Enantioselective C-H Arylation of Indoles
    Jacob, Nicolas
    Zaid, Yassir
    Oliveira, Joao C. A.
    Ackermann, Lutz
    Wencel-Delord, Joanna
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (02) : 798 - 806
  • [45] Enantioselective Cobalt(III)-Catalyzed C-H Activation Enabled by Chiral Carboxylic Acid Cooperation
    Pesciaioli, Fabio
    Dhawa, Uttam
    Oliveira, Joao C. A.
    Yin, Rongxin
    John, Michael
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (47) : 15425 - 15429
  • [46] Nickel(II)/Salox-Catalyzed Enantioselective C-H Functionalization
    Chen, Jia-Hao
    Yao, Qi-Jun
    Zhong, Ming-Yu
    Jiang, Tian-Yu
    Huang, Fan-Rui
    Li, Xiang
    Shi, Bing-Feng
    ACS CENTRAL SCIENCE, 2025, 11 (01) : 127 - 135
  • [47] Recent advances in Rh(I)-catalyzed enantioselective C-H functionalization
    Zhang, Yue
    Zhang, Jing-Jing
    Lou, Lujun
    Lin, Ruofan
    Cramer, Nicolai
    Wang, Shou-Guo
    Chen, Zhen
    CHEMICAL SOCIETY REVIEWS, 2024, 53 (07) : 3457 - 3484
  • [48] Three-component regioselective carboamidation of 1,3-enynes via rhodium(iii)-catalyzed C-H activation
    Kong, Lingheng
    Han, Xi
    Hu, Panjie
    Wang, Fen
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2023, 59 (44) : 6690 - 6693
  • [49] Rhodium(I)-Catalyzed Direct Enantioselective C-H Functionalization of Indoles
    Zhu, Dong-Xing
    Xu, Ming-Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (12): : 7844 - 7848
  • [50] Cobalt(III)-Catalyzed Directed C-H Allylation
    Gensch, Tobias
    Vasquez-Cespedes, Suhelen
    Yu, Da-Gang
    Glorius, Frank
    ORGANIC LETTERS, 2015, 17 (15) : 3714 - 3717