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

[111] An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions [J].

Valizadeh, H ;

Shockravi, A .

TETRAHEDRON LETTERS, 2005, 46 (20) :3501-3503

[112] Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates;: an enantioselective route to β-aryl-nitroalkanes [J].

Versleijen, JPG ;

van Leusen, AM ;

Feringa, BL .

TETRAHEDRON LETTERS, 1999, 40 (31) :5803-5806

[113] An Enantioselective Approach to Highly Substituted Tetrahydrocarbazoles through Hydrogen Bonding-Catalyzed Cascade Reactions [J].

Wang, Xu-Fan ;

Chen, Jia-Rong ;

Cao, Yi-Ju ;

Cheng, Hong-Gang ;

Xiao, Wen-Jing .

ORGANIC LETTERS, 2010, 12 (05) :1140-1143

[114] Asymmetric Diels-Alder reactions of 2-pyrones with a bifunctional organic catalyst [J].

Wang, Yi ;

Li, Hongming ;

Wang, Yong-Qiang ;

Liu, Yan ;

Foxman, Bruce M. ;

Deng, Li .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (20) :6364-+

[115] Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins [J].

Waser, Jerome ;

Gaspar, Boris ;

Nambu, Hisanori ;

Carreira, Erick M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) :11693-11712

[116] Frontiers in organic synthesis: Introduction [J].

Wender, PA .

CHEMICAL REVIEWS, 1996, 96 (01) :1-2

[117] Synthesis at the molecular frontier [J].

Wender, Paul A. ;

Miller, Benjamin L. .

NATURE, 2009, 460 (7252) :197-201

[118] Enantioselective organocatalytic intramolecular Diels-Alder reactions. The asymmetric synthesis of solanapyrone D [J].

Wilson, RM ;

Jen, WS ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11616-11617

[119] Efficient method for the synthesis of functionalized pyrazoles by catalyst-free one-pot tandem reaction of nitroalkenes with ethyl diazoacetate [J].

Xie, Jian-Wu ;

Wang, Zheng ;

Yang, Wei-Jun ;

Kong, Li-Chun ;

Xu, Dong-Cheng .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (21) :4352-4354

[120] Chiral Squaramides as Highly Enantioselective Catalysts for Michael Addition Reactions of 4-Hydroxycoumarins and 4-Hydroxypyrone to β,γ-Unsaturated α-Keto Esters [J].

Xu, Dan-Qian ;

Wang, Yi-Feng ;

Zhang, Wei ;

Luo, Shu-Ping ;

Zhong, Ai-Guo ;

Xia, Ai-Bao ;

Xu, Zhen-Yuan .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) :4177-4180

← 4 5 6 7 8 9 10 11 12 13 →