Enantioselective Synthesis of Axially Chiral Benzimidazoles Bearing a C-N axis via Pd-Catalyzed Buchwald-Hartwig-Amination

被引:6
作者
Zhang, Peng [1 ]
Feng, Jia [1 ]
Uu, Ren-rong [1 ]
机构
[1] Qingdao Univ, Coll Chem & Chem Engn, Ningxia Rd 308, Qingdao 266071, Peoples R China
关键词
atropisomerism; palladium; amination; benzimidazole atropisomers; asymmetric catalysis; STEREOSELECTIVE-SYNTHESIS; ATROPISOMERIC ANILIDES; ARYL HALIDES; CONSTRUCTION; RESOLUTION; CHEMISTRY; ARYLATION; CHLORIDES; INDOLES; BONDS;
D O I
10.1055/a-1833-8979
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzimidazole atropisomers bearing a C-N axis are privileged structural frameworks in pharmaceutical and natural products, thus appealing an increasing interest for its asymmetric synthesis. Here, we briefly discuss recent advances in the asymmetric synthesis of benzimidazole atropisomers with a C-N axis, with particular attention to our recently developed palladium-catalyzed intramolecular Buchwald-Hartwig amination strategy.
引用
收藏
页码:1589 / 1595
页数:7
相关论文
共 63 条
[1]   Nitrosobenzene-Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N-Arylbenzimidazoles [J].
An, Qian-Jin ;
Xia, Wang ;
Ding, Wei-Yi ;
Liu, Huan-Huan ;
Xiang, Shao-Hua ;
Wang, Yong-Bin ;
Zhong, Guofu ;
Tan, Bin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (47) :24888-24893
[2]   C-N bond forming cross-coupling reactions: an overview [J].
Bariwal, Jitender ;
Van der Eycken, Erik .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303
[3]   Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation [J].
Bhunia, Subhajit ;
Pawar, Govind Goroba ;
Kumar, S. Vijay ;
Jiang, Yongwen ;
Ma, Dawei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16136-16179
[4]  
Bock L.H., 1931, J Am Chem Soc, V53, P374, DOI DOI 10.1021/JA01352A055
[5]   Stereochemistry of phenyl pyrroles. XIX [J].
Bock, LH ;
Adams, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1931, 53 :3519-3522
[6]   Murrastifoline-F:: First total synthesis, atropo-enantiomer resolution, and stereoanalysis of an axially chiral N,C-coupled biaryl alkaloid [J].
Bringmann, G ;
Tasler, S ;
Endress, H ;
Kraus, J ;
Messer, K ;
Wohlfarth, M ;
Lobin, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2703-2711
[7]   Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].
Bringmann, Gerhard ;
Gulder, Tanja ;
Gulder, Tobias A. M. ;
Breuning, Matthias .
CHEMICAL REVIEWS, 2011, 111 (02) :563-639
[8]   Recent Advances in Catalytic Asymmetric Construction of Atropisomers [J].
Cheng, Jun Kee ;
Xiang, Shao-Hua ;
Li, Shaoyu ;
Ye, Liu ;
Tan, Bin .
CHEMICAL REVIEWS, 2021, 121 (08) :4805-4902
[9]   The molecular configurations of polynuclear aromatic compounds. Part I. The resolution of gamma-6 : 6'-dinitro- and 4 : 6 : 4': 6'-tetranitro-diphenic acids into optically active components. [J].
Christie, GH ;
Kenner, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1922, 121 :614-620
[10]   C-N atropopure compounds: New directions [J].
Colobert, Francoise ;
Shi, Bing-Feng .
CHEM CATALYSIS, 2021, 1 (03) :483-485