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
  • [31] Synthesis of Chiral Diarylmethylamines by Cobalt-Catalyzed Enantioselective C-H Alkoxylation
    Wang, Zhen-Kai
    Wu, Yong-Jie
    Yao, Qi-Jun
    Shi, Bing-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)
  • [32] 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
  • [33] An Enantioselective CpxRh(III)-Catalyzed C-H Functionalization/Ring-Opening Route to Chiral Cyclopentenylamines
    Wang, Shou-Guo
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (08) : 2514 - 2518
  • [34] C3 functionalization of indolizines via In(III)-catalyzed three-component reaction
    Jung, Youngeun
    Kim, Ikyon
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (45) : 10986 - 10994
  • [35] Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C-H Functionalization and Spiroannulation
    Chidipudi, Suresh Reddy
    Burns, David J.
    Khan, Imtiaz
    Lam, Hon Wai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 13975 - 13979
  • [36] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [37] Enantioselective C-H functionalization reactions enabled by cobalt catalysis
    Zheng, Yang
    Zheng, Chao
    Gu, Qing
    You, Shu-Li
    CHEM CATALYSIS, 2022, 2 (11): : 2965 - 2985
  • [38] Forging C-heteroatom bonds by transition-metal-catalyzed enantioselective C-H functionalization
    Zhang, Qi
    Wu, Le-Song
    Shi, Bing-Feng
    CHEM, 2022, 8 (02): : 384 - 413
  • [39] Mild Cobalt(III)-Catalyzed Allylative C-F/C-H Functionalizations at Room Temperature
    Zell, Daniel
    Mueller, Valentin
    Dhawa, Uttam
    Bursch, Markus
    Presa, Ruben Rubio
    Grimme, Stefan
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12145 - 12148
  • [40] Selective Synthesis of Indoles by Cobalt(III)-Catalyzed C-H/N-O Functionalization with Nitrones
    Wang, Hui
    Moselage, Marc
    Gonzalez, Maria J.
    Ackermann, Lutz
    ACS CATALYSIS, 2016, 6 (04): : 2705 - 2709