Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization

被引:196
作者
Achar, Tapas Kumar [1 ]
Maiti, Sudip [1 ]
Jana, Sadhan [1 ]
Maiti, Debabrata [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
关键词
asymmetric catalysis; C-H activation; desymmetrization; axial chirality; artificial metalloenzymes; C-H ACTIVATION; PLANAR CHIRAL FERROCENES; PROTON-ABSTRACTION MECHANISM; TRANSIENT DIRECTING GROUPS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; KINETIC RESOLUTION; C(SP(3))-H BONDS; DIRECT ARYLATION; BIARYL COMPOUNDS;
D O I
10.1021/acscatal.0c03743
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
Direct catalytic transformation of C-H bonds to new functionalities has provided a powerful strategy to synthesize complex molecular scaffolds in a straightforward way. Unstinting efforts of the synthetic community have helped to overcome the long-standing major challenge of regioselectivity by introducing the directing group concept. However, the full potential of the strategy cannot be realized unless the activated C-H bonds are stereochemically controlled. The enantioselective C-H bond functionalization could provide an imperative tool for a sustainable way of synthesizing chiral complex molecular scaffolds. Despite the intrinsic challenges in achieving stereocontrol, the synthetic community has developed different tools in order to achieve stereoselective C-H bond functionalization. In this review, we discuss the remarkable recent advances in the emerging area of enantioselective C(sp(2))-H bond functionalization to highlight the challenges and opportunities, emphasizing the different techniques developed so far.
引用
收藏
页码:13748 / 13793
页数:46
相关论文
共 276 条
  • [1] Palladium-Catalyzed Directed meta-Selective C-H Allylation of Arenes: Unactivated Internal Olefins as Allyl Surrogates
    Achar, Tapas Kumar
    Zhang, Xinglong
    Mondal, Rahul
    Shanavas, M. S.
    Maiti, Siddhartha
    Maity, Sabyasachi
    Pal, Nityananda
    Paton, Robert S.
    Maiti, Debabrata
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (30) : 10353 - 10360
  • [2] Robust Ruthenium(II)-Catalyzed C-H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers
    Ackermann, Lutz
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) : 260 - 269
  • [3] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [4] The stereochemistry of diphenyls and analogous compounds
    Adams, R
    Yuan, HC
    [J]. CHEMICAL REVIEWS, 1933, 12 (02) : 261 - 338
  • [5] Orthogonal Selectivity in C-H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution
    Agasti, Soumitra
    Mondal, Bhaskar
    Achar, Tapas Kumar
    Sinha, Soumya Kumar
    Suseelan, Anjana Sarala
    Szabo, Kalman J.
    Schoenebeck, Franziska
    Maiti, Debabrata
    [J]. ACS CATALYSIS, 2019, 9 (10): : 9606 - 9613
  • [6] Nickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones
    Ahlin, Joachim S. E.
    Donets, Pavel A.
    Cramer, Nicolai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) : 13229 - 13233
  • [7] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [8] Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters
    Albicker, Martin R.
    Cramer, Nicolai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) : 9139 - 9142
  • [9] A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups
    Annapureddy, Rajasekar Reddy
    Jandl, Christian
    Bach, Thorsten
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) : 7374 - 7378
  • [10] [Anonymous], 2002, TOP CURR CHEM