Synthesis of Atropisomers by Transition-Metal-Catalyzed Asymmetric C-H Functionalization Reactions

被引:250
|
作者
Liu, Chen-Xu [1 ]
Zhang, Wen-Wen [2 ]
Yin, Si-Yong [1 ]
Gu, Qing [1 ]
You, Shu-Li [1 ,2 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] East China Normal Univ, Chang Kung Chuang Inst, Shanghai 200062, Peoples R China
关键词
DYNAMIC KINETIC RESOLUTION; AXIALLY CHIRAL BIARYLS; ENANTIOSELECTIVE SYNTHESIS; ATROPOSELECTIVE SYNTHESIS; C(SP(3))-H BONDS; FACILE SYNTHESIS; ACTIVATION; CONSTRUCTION; OLEFINATION; ARYLATION;
D O I
10.1021/jacs.1c07635
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition-metal-catalyzed enantioselective C-H functionalization has become a powerful strategy for the formation of C-C or C-X bonds, enabling the highly asymmetric synthesis of a wide range of enantioenriched compounds. Atropisomers are widely found in natural products and pharmaceutically relevant molecules, and have also found applications as privileged frameworks for chiral ligands and catalysts. Thus, research into asymmetric routes for the synthesis of atropisomers has garnered great interest in recent years. In this regard, transition-metal-catalyzed enantioselective C-H functionalization has emerged as an atom-economic and efficient strategy toward their synthesis. In this Perspective, the approaches for the synthesis of atropisomers by transition-metal-catalyzed asymmetric C-H functionalization reactions are summarized. The main focus here is on asymmetric catalysis via Pd, Rh, and Ir complexes, which have been the most frequently utilized catalysts among reported enantioselective C-H functionalization reactions. Finally, we discuss limitations on available protocols and give an outlook on possible future avenues of research.
引用
收藏
页码:14025 / 14040
页数:16
相关论文
共 50 条
  • [21] Recent Advances in Transition-Metal-Catalyzed C-H Functionalization of Ferrocene Amides
    Mou, Qi
    Zhao, Ruyuan
    Sun, Bo
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (21)
  • [22] Transition-metal-catalyzed C-H bond activation/functionalization and annulation of phthalazinones
    Sivaraj, Chandrasekaran
    Ramkumar, Alagumalai
    Sankaran, Nagesh
    Gandhi, Thirumanavelan
    Organic and Biomolecular Chemistry, 2021, 19 (38): : 8165 - 8183
  • [23] Transition-metal-catalyzed ortho C-H functionalization of 2-arylquinoxalines
    Mondal, Koushik
    Ghosh, Sumit
    Hajra, Alakananda
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (37) : 7361 - 7376
  • [24] Transition-Metal-Catalyzed C-H Functionalization for Construction of Quaternary Carbon Centers
    Li, Yang
    Xu, Silong
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (61) : 16218 - 16245
  • [25] Transition-metal-catalyzed C-H bond activation/functionalization and annulation of phthalazinones
    Sivaraj, Chandrasekaran
    Ramkumar, Alagumalai
    Sankaran, Nagesh
    Gandhi, Thirumanavelan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8165 - 8183
  • [26] Advances in Transition-Metal-Catalyzed Keto Carbonyl-Directed C-H Bond Functionalization Reactions
    Chen Silin
    Yang Yunhui
    Chen Chao
    Wang Congyang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (01) : 1 - 16
  • [27] Recent Advances in Transition-Metal-Catalyzed C-H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes
    Sihag, Pinki
    Jeganmohan, Masilamani
    SYNTHESIS-STUTTGART, 2021, 53 (18): : 3249 - 3262
  • [28] Transition-Metal-Catalyzed C-H Alkynylation
    Wang, Mingming
    Wang, Zixiao
    Shang, Ming
    Dai, Huixiong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (03) : 570 - 577
  • [29] Transition-Metal-Catalyzed Hydroarylation Reactions of Alkynes Through Direct Functionalization of C-H Bonds: A Convenient Tool for Organic Synthesis
    Kitamura, Tsugio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (08) : 1111 - 1125
  • [30] Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization
    Huang, Jianpian
    Gu, Qing
    You, Shuli
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (01) : 51 - 61