Recent Advances in Catalytic Asymmetric Construction of Atropisomers

被引:694
作者
Cheng, Jun Kee [1 ,2 ]
Xiang, Shao-Hua [1 ,2 ,3 ]
Li, Shaoyu [1 ,2 ,3 ]
Ye, Liu [1 ,2 ,3 ]
Tan, Bin [1 ,2 ]
机构
[1] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
[2] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
[3] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
DYNAMIC-KINETIC RESOLUTION; AXIALLY CHIRAL BIARYLS; ALDOL CONDENSATION SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ATROPOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; COUPLING REACTIONS; RATIONAL DESIGN; INTRAMOLECULAR HYDROARYLATION; BIFUNCTIONAL ORGANOCATALYSTS;
D O I
10.1021/acs.chemrev.0c01306
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Atropisomerism is a stereochemical behavior portrayed by three-dimensional molecules that bear rotationally restricted sigma bond. Akin to the well-represented point-chiral molecules, atropisomerically chiral compounds are finding increasing utilities in many disciplines where molecular asymmetry is influential. This provides steady demand on atroposelective synthesis, where numerous synthetic pursuits have been rewarded with conceptually novel and streamlined methods while expanding the structural diversity of atropisomers. This review summarizes key achievements in stereoselective preparation of biaryl, heterobiaryl, and nonbiaryl atropisomers documented between 2015 and 2020. Emphasis is placed on the synthetic strategies for each structural class, while examples are cited to illustrate the potential applications of the accessed atropochiral targets.
引用
收藏
页码:4805 / 4902
页数:98
相关论文
共 292 条
[61]   Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols [J].
Egami, Hiromichi ;
Katsuki, Tsutomu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6082-+
[62]   Artificial Molecular Machines [J].
Erbas-Cakmak, Sundus ;
Leigh, David A. ;
McTernan, Charlie T. ;
Nussbaumer, Alma L. .
CHEMICAL REVIEWS, 2015, 115 (18) :10081-10206
[63]   Organocatalytic Atroposelective Formal Diels-Alder Desymmetrization of N-Arylmaleimides [J].
Eudier, Florine ;
Righi, Paolo ;
Mazzanti, Andrea ;
Ciogli, Alessia ;
Bencivenni, Giorgio .
ORGANIC LETTERS, 2015, 17 (07) :1728-1731
[64]   Asymmetric Total Synthesis of TAN-1085 Facilitated by Pd-Catalyzed Atroposelective C-H Olefination [J].
Fan, Jun ;
Yao, Qi-Jun ;
Liu, Yan-Hua ;
Liao, Gang ;
Zhang, Shuo ;
Shi, Bing-Feng .
ORGANIC LETTERS, 2019, 21 (09) :3352-3356
[65]   Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed Intramolecular Adjacent C-N Coupling [J].
Fan, Xiaozhong ;
Zhang, Xue ;
Li, Chunyu ;
Gu, Zhenhua .
ACS CATALYSIS, 2019, 9 (03) :2286-+
[66]   Asymmetric Synthesis of Axially Chiral Isoquinolones: Nickel-Catalyzed Denitrogenative Transannulation [J].
Fang, Zhi-Jia ;
Zheng, Sheng-Cai ;
Guo, Zhen ;
Guo, Jing-Yao ;
Tan, Bin ;
Liu, Xin-Yuan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) :9528-9532
[67]   Stereoselective Arene-Forming Aldol Condensation: Synthesis of Axially Chiral Aromatic Amides [J].
Faseke, Vincent C. ;
Sparr, Christof .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) :7261-7264
[68]   Enantioselective Synthesis of Atropisomeric Vinyl Arene Compounds by Palladium Catalysis: A Carbene Strategy [J].
Feng, Jia ;
Li, Bin ;
He, Yun ;
Gu, Zhenhua .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (06) :2186-2190
[69]   Enantioselective Synthesis of N-C Axially Chiral Compounds by Cu-Catalyzed Atroposelective Aryl Amination [J].
Frey, Johanna ;
Malekafzali, Alaleh ;
Delso, Isabel ;
Choppin, Sabine ;
Colobert, Francoise ;
Wencel-Delord, Joanna .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) :8844-8848
[70]   Hydrogen-Bond-Enabled Dynamic Kinetic Resolution of Axially Chiral Amides Mediated by a Chiral Counterion [J].
Fugard, Alison J. ;
Lahdenpera, Antti S. K. ;
Tan, Jaqueline S. J. ;
Mekareeya, Aroonroj ;
Paton, Robert S. ;
Smith, Martin D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (09) :2795-2798