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

被引:207
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
[91]   Atroposelective Synthesis of Axially Chiral Styrenes via an Asymmetric C-H Functionalization Strategy [J].
Jin, Liang ;
Yao, Qi-Jun ;
Xie, Pei-Pei ;
Li, Ya ;
Zhan, Bei-Bei ;
Han, Ye-Qiang ;
Hong, Xin ;
Shi, Bing-Feng .
CHEM, 2020, 6 (02) :497-511
[92]   More than bystanders: The effect of Olefins on transition-metal-catalyzed cross-coupling reactions [J].
Johnson, Jeffrey B. ;
Rovis, Tomislav .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (05) :840-871
[93]   Atropselective alkylation of biaryl compounds by means of transition metal-catalyzed C-H/olefin coupling [J].
Kakiuchi, F ;
Le Gendre, P ;
Yamada, A ;
Ohtaki, H ;
Murai, S .
TETRAHEDRON-ASYMMETRY, 2000, 11 (13) :2647-2651
[94]   Asymmetric C-H functionalization of cyclopropanes using an isoleucine-NH2 bidentate directing group [J].
Kim, Jinhee ;
Sim, Mikyung ;
Kim, Namhoon ;
Hong, Sungwoo .
CHEMICAL SCIENCE, 2015, 6 (06) :3611-3616
[95]   Non-symmetrically substituted 1,1′-binaphthyls in enantioselective catalysis [J].
Kocovsky, P ;
Vyskocil, S ;
Smrcina, M .
CHEMICAL REVIEWS, 2003, 103 (08) :3213-3245
[96]   Rhodium(III)-Catalyzed Asymmetric Access to Spirocycles through C-H Activation and Axial-to-Central Chirality Transfer [J].
Kong, Lingheng ;
Han, Xi ;
Liu, Song ;
Zou, Yun ;
Lan, Yu ;
Li, Xingwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (18) :7188-7192
[97]   Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole [J].
Kong, Wangqing ;
Wang, Qian ;
Zhu, Jieping .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (51) :16028-16031
[98]   Bulky chiral carbene ligands and their application in the palladium-catalyzed asymmetric intramolecular α-arylation of amides [J].
Kuendig, E. Peter ;
Seidel, Thomas M. ;
Jia, Yi-Xia ;
Bernardinelli, Gerald .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) :8484-8487
[99]   Beyond Directing Groups: Transition-Metal-Catalyzed C-H Activation of Simple Arenes [J].
Kuhl, Nadine ;
Hopkinson, Matthew N. ;
Wencel-Delord, Joanna ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10236-10254
[100]   Rhodium-Catalyzed Asymmetric Synthesis of Spirosilabifluorene Derivatives [J].
Kuninobu, Yoichiro ;
Yamauchi, Kanae ;
Tamura, Naoya ;
Seiki, Takayuki ;
Takai, Kazuhiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1520-1522