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

被引:206
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 [J].
Achar, Tapas Kumar ;
Zhang, Xinglong ;
Mondal, Rahul ;
Shanavas, M. S. ;
Maiti, Siddhartha ;
Maity, Sabyasachi ;
Pal, Nityananda ;
Paton, Robert S. ;
Maiti, Debabrata .
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 [J].
Ackermann, Lutz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) :260-269
[3]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[4]   The stereochemistry of diphenyls and analogous compounds [J].
Adams, R ;
Yuan, HC .
CHEMICAL REVIEWS, 1933, 12 (02) :261-338
[5]   Orthogonal Selectivity in C-H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution [J].
Agasti, Soumitra ;
Mondal, Bhaskar ;
Achar, Tapas Kumar ;
Sinha, Soumya Kumar ;
Suseelan, Anjana Sarala ;
Szabo, Kalman J. ;
Schoenebeck, Franziska ;
Maiti, Debabrata .
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 [J].
Ahlin, Joachim S. E. ;
Donets, Pavel A. ;
Cramer, Nicolai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) :13229-13233
[7]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[8]   Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].
Albicker, Martin R. ;
Cramer, Nicolai .
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 [J].
Annapureddy, Rajasekar Reddy ;
Jandl, Christian ;
Bach, Thorsten .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) :7374-7378
[10]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]