Bronsted acid catalyzed Diels-Alder reactions of 2-vinylindoles and 3-nitrocoumarins: an expedient synthesis of coumarin-fused tetrahydrocarbazoles

被引：34
作者：
Tan, Fen [1 ]
Li, Fang [1 ]
Zhang, Xiao-Xiao [1 ]
Wang, Xu-Fan [1 ]
Cheng, Hong-Gang [1 ]
Chen, Jia-Rong [1 ]
Xiao, Wen-Jing [1 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 02期
基金：
美国国家科学基金会;
关键词：
Organocatalysis; Diels-Alder reaction; Coumarin; Tetrahydrocarbazole; INVERSE-ELECTRON-DEMAND; FRIEDEL-CRAFTS ALKYLATION; SIMPLE INDOLE ALKALOIDS; EFFICIENT ROUTE; ALPHA; BETA-UNSATURATED ALDEHYDES; SULFUR YLIDES; ORGANIC CATALYSIS; DERIVATIVES; ACTIVATION; ORGANOCATALYSIS;
D O I：
10.1016/j.tet.2010.11.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Bronsted acid catalyzed Diels-Alder reaction of 2-vinylindoles and 3-nitrocoumarins has been described. The methodology allows a rapid and expedient synthesis of a variety of coumarin-fused polycyclic indoles in good yields (up to 82%) with high diastereoselectivities (up to >19:1). (C) 2010 Published by Elsevier Ltd.
引用
收藏
页码：446 / 451
页数：6
相关论文
共 128 条
[71]  
2-T
[72]   Chiral oxazaborolidine-aluminum bromide complexes are unusually powerful and effective catalysts for enantioselective Diels-Alder reactions [J].
Liu, Duan ;
Canales, Eda ;
Corey, E. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1498-+
[73]   Catalytic Asymmetric Intramolecular Hydroarylations of ω-Aryloxy- and Arylamino-Tethered α,β-Unsaturated Aldehydes [J].
Lu, Hai-Hua ;
Liu, Hui ;
Wu, Wei ;
Wang, Xu-Fan ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (12) :2742-2746
[74]   A new entry to cascade organocatalysis: Reactions of stable sulfur ylides and nitroolefins sequentially catalyzed by thiourea and DMAP [J].
Lu, Liang-Qiu ;
Cao, Yi-Ju ;
Liu, Xiao-Peng ;
An, Jing ;
Yao, Chang-Jiang ;
Ming, Zhi-Hui ;
Xiao, Wen-Jing .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) :6946-+
[75]   Tuning Electronic and Steric Effects: Highly Enantioselective [4+1] Pyrroline Annulation of Sulfur Ylides with α,β-Unsaturated Imines [J].
Lu, Liang-Qiu ;
Zhang, Ji-Ji ;
Li, Fang ;
Cheng, Ying ;
An, Jing ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (26) :4495-4498
[76]   Construction of Fused Heterocyclic Architectures by Formal [4+1]/[3+2] Cycloaddition Cascade of Sulfur Ylides and Nitroolefins [J].
Lu, Liang-Qiu ;
Li, Fang ;
An, Jing ;
Zhang, Ji-Ji ;
An, Xiao-Lei ;
Hua, Qiu-Lin ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9542-9545
[77]   Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions [J].
Ma, JA ;
Cahard, D .
CHEMICAL REVIEWS, 2004, 104 (12) :6119-6146
[78]   The advent and development of organocatalysis [J].
MacMillan, David W. C. .
NATURE, 2008, 455 (7211) :304-308
[79]  
Maruoka K., 2000, Catalytic Asymmetric Synthesis, V2nd, P467
[80]   Enantioselective Organocatalytic Diels-Alder Reactions [J].
Merino, Pedro ;
Marques-Lopez, Eugenia ;
Tejero, Tomas ;
Herrera, Raquel P. .
SYNTHESIS-STUTTGART, 2010, (01) :1-26
3456789101112