Construction of Chiral Tricyclic Indoles through a Rhodium-Catalyzed Asymmetric Arylation Protocol

被引：27

作者：

Wu, Chun-Yan

Yu, Yue-Na

Xu, Ming-Hua ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 02期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE CONSTRUCTION; ARYLBORONIC ACIDS; BORONIC ACIDS; DIENE LIGANDS; 1,4-ADDITION; STEREOCENTERS; DERIVATIVES; OLEFINS; POTENT; ARYL;

D O I：

10.1021/acs.orglett.6b03585

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium/diene complex catalyzed asymmetric 1,4-addition of arylboronic acids to indole-derived alpha,beta-unsaturated esters to access highly enantioenriched 3-(1H-indol-2-yl)-3-arylpropanoates has been developed. By taking advantage of the nucleophilic character of indole at C3 and N1 positions, construction of a series of valuable chiral tricyclic indole frameworks such as 2,3-dihydro-1H-pyrrolo[1,2-a]indoles and cyclopenta[b]indoles can be efficiently achieved.

引用

页码：384 / 387

页数：4

共 48 条

[1] Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands [J].

Boiteau, JG ;

Imbos, F ;

Minnaard, AJ ;

Feringa, BL .

ORGANIC LETTERS, 2003, 5 (05) :681-684

[2] Reserpine: A challenge for total synthesis of natural products [J].

Chen, FE ;

Huang, J .

CHEMICAL REVIEWS, 2005, 105 (12) :4671-4706

[3] Highly Enantioselective Friedel-Crafts Alkylation/N-Hemiacetalization Cascade Reaction with Indoles [J].

Cheng, Hong-Gang ;

Lu, Liang-Qiu ;

Wang, Tao ;

Yang, Qing-Qing ;

Liu, Xiao-Peng ;

Li, Yang ;

Deng, Qiao-Hui ;

Chen, Jia-Rong ;

Xiao, Wen-Jing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3250-3254

[4] BIOMIMETIC SYNTHESIS OF YEUHCHUKENE [J].

CHENG, KF ;

KONG, YC ;

CHAN, TY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (02) :48-49

[5] Chiral olefins as steering ligands in asymmetric catalysis [J].

Defieber, Christian ;

Gruetzmacher, Hansjoerg ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502

[6] Expedient synthesis of densely substituted pyrrolo[1,2-a]indoles [J].

Dethe, Dattatraya H. ;

Boda, Raghavender .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) :5843-5860

[7] Quadruple Domino Organocatalysis: An Asymmetric Aza-Michael/Michael/Michael/Aldol Reaction Sequence Leading to Tetracyclic Indole Structures with Six Stereocenters [J].

Enders, Dieter ;

Greb, Andreas ;

Deckers, Kristina ;

Selig, Philipp ;

Merkens, Carina .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (33) :10226-10229

[8] One-Pot Organocatalytic Asymmetric Synthesis of 1H-Pyrrolo[1,2a]indol-3(2H)-ones via a Michael-Hemiaminalization-Oxidation Sequence [J].

Enders, Dieter ;

Wang, Chuan ;

Yang, Xuena ;

Raabe, Gerhard .

SYNLETT, 2011, (04) :469-472

[9] The Application of N-Protected 3-Vinylindoles in Chiral Phosphoric Acid-Catalyzed [3+2] Cyclization with 3-Indolylmethanols: Monoactivation of the Catalyst to Vinyliminium [J].

Fan, Tao ;

Zhang, Hong-Hao ;

Li, Can ;

Shen, Yang ;

Shi, Feng .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (12) :2017-2031

[10] Easily accessible C2-symmetric chiral bicyclo[3.3.0] dienes as ligands for rhodium-catalyzed asymmetric 1,4-addition [J].

Feng, Chen-Guo ;

Wang, Zhi-Qian ;

Tian, Ping ;

Xu, Ming-Hua ;

Lin, Guo-Qiang .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) :1511-1516

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