Rh(III)-Catalyzed Asymmetric Synthesis of Axially Chiral Biindolyls by Merging C-H Activation and Nucleophilic Cyclization

被引：225

作者：

Tian, Miaomiao ^{[1
]}

Bai, Dachang ^{[1
]}

Zheng, Guangfan ^{[2
]}

Chang, Junbiao ^{[1
]}

Li, Xingwei ^{[1
,2
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Henan, Peoples R China

[2] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710062, Shaanxi, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 24期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ATROPOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; LIGANDS; RHODIUM; CONSTRUCTION; ATROPISOMERS; CATALYSIS; INDOLES; FUNCTIONALIZATION;

D O I：

10.1021/jacs.9b04711

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomeric access to pentatomic biaryls is challenging due to their relatively low rotational barrier. Reported herein is the mild and highly enantioselective synthesis of 2,3'-biindolyls via underexplored integration of C-H activation and alkyne cyclization using a unified chiral Rh(III) catalyst. The reaction proceeded via initial C-H activation followed by alkyne cyclization. A chiral rhodacyclic intermediate has been isolated from stoichiometric C-H activation, which offers direct mechanistic insight.

引用

页码：9527 / 9532

页数：6

共 50 条

[1] Rh-Catalyzed Asymmetric C-H Activation for the Synthesis of Planar Chiral Ferrocenes
Duan, Wei-Liang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (12) : 3598 - 3599
[2] Merging C-H and C-C Activation in Pd(II)-Catalyzed Enantioselective Synthesis of Axially Chiral Biaryls
Chen, Hao-Ming
Liao, Gang
Xu, Cheng-Kai
Yao, Qi-Jun
Zhang, Shuo
Shi, Bing-Feng
CCS CHEMISTRY, 2021, 3 (12): : 455 - 465
[3] Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines
Chen, Renjie
Qi, Jifeng
Mao, Zhenjun
Cui, Sunliang
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (26) : 6201 - 6204
[4] Rh(III)-Catalyzed C-H Activation/Cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles
Zhang, Yan
Zheng, Jing
Cui, Sunliang
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14): : 6490 - 6500
[5] Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C-H Functionalizations
Ye, Baihua
Cramer, Nicolai
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) : 1308 - 1318
[6] Rhodium(III)-Catalyzed Atroposelective Synthesis of C-N Axially Chiral Naphthylamines and Variants via C-H Activation
Wang, Peiyuan
Huang, Yaling
Jing, Jierui
Wang, Fen
Li, Xingwei
ORGANIC LETTERS, 2022, 24 (13) : 2531 - 2535
[7] Synthesis of axially chiral biaryl thioglycosides through thiosugar-directed Pd-catalyzed asymmetric C-H activation
Fatthalla, Maha
Grimblat, Nicolas
Brachet, Etienne
Alami, Mouad
Gandon, Vincent
Le Bideau, Franck
Messaoudi, Samir
CHEMICAL COMMUNICATIONS, 2021, 57 (80) : 10355 - 10358
[8] Rh(III)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C-H activation
Shi, Zhuangzhi
Boultadakis-Arapinis, Melissa
Koester, Dennis C.
Glorius, Frank
CHEMICAL COMMUNICATIONS, 2014, 50 (20) : 2650 - 2652
[9] Rh(III)-catalyzed C-H activation/cyclization of benzamides and diazo compounds to form isocoumarins and α-pyrones
Li, Xing Guang
Sun, Min
Liu, Kai
Jin, Qiao
Liu, Pei Nian
CHEMICAL COMMUNICATIONS, 2015, 51 (12) : 2380 - 2383
[10] Rh(III)-Catalyzed Cascade Oxidative Olefination/Cyclization of Picolinamides and Alkenes via C-H Activation
Cai, Shangun
Chen, Chao
Shao, Peng
Xi, Chanjuan
ORGANIC LETTERS, 2014, 16 (11) : 3142 - 3145

← 1 2 3 4 5 →