Catalytic Asymmetric Aza-Michael-Michael Addition Cascade: Enantioselective Synthesis of Polysubstituted 4-Aminobenzopyrans

被引：88

作者：

Wang, Xu-Fan ^{[1
]}

An, Jing ^{[1
]}

Zhang, Xiao-Xiao ^{[1
]}

Tan, Fen ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Minist Educ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 04期

基金：

美国国家科学基金会;

关键词：

DIELS-ALDER REACTIONS; DIASTEREOSELECTIVE SYNTHESIS; SULFUR YLIDES; ANTIHYPERTENSIVE ACTIVITY; FUSED PYRANOBENZOPYRANS; BIFUNCTIONAL THIOUREA; NATURAL-PRODUCTS; ALDOL REACTIONS; FURANOBENZOPYRANS; GENERATION;

D O I：

10.1021/ol1031188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric aza-Michael-Michael addition cascade of anilines to nitroolefin enoates in the presence of chiral bifunctional thiourea catalysts has been disclosed. This reaction provides a mild and efficient approach to polysubstituted chiral 4-aminobenzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities.

引用

页码：808 / 811

页数：4

共 58 条

[1] Indium(III) chloride catalyzed in situ generation of enamines and cyclization with imines:: a novel route for synthesis of hexahydroxanthene-9-N-arylamines
Anniyappan, M
Muralidharan, D
Perumal, PT
Vittal, JJ
[J]. TETRAHEDRON, 2004, 60 (13) : 2965 - 2969
[2] Diastereoselective synthesis of cis-fused pyrano and furanobenzopyrans catalyzed by indium trichloride or triphenyl phosphonium perchlorate
Anniyappan, M
Muralidharan, D
Perumal, PT
[J]. TETRAHEDRON, 2002, 58 (52) : 10301 - 10307
[3] [Anonymous], 1977, CHROMENES CHROMANSSE
[4] Catalytic Asymmetric Inverse-Electron-Demand (IED) [4+2] Cycloaddition of Salicylaldimines: Preparation of Optically Active 4-Aminobenzopyran Derivatives
Bernardi, Luca
Comes-Franchini, Mauro
Fochi, Mariafrancesca
Leo, Virginia
Mazzanti, Andrea
Ricci, Alfredo
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3399 - 3406
[5] Catalytic enantioselective synthesis of flavanones and chromanones
Biddle, Margaret M.
Lin, Michael
Scheidt, Karl A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) : 3830 - +
[6] RELAXANT ACTIVITY OF 4-AMIDO-3,4-DIHYDRO-2H-1-BENZOPYRAN-3-OLS AND 4-AMIDO-2H-1-BENZOPYRANS ON GUINEA-PIG ISOLATED TRACHEALIS
BUCKLE, DR
ARCH, JRS
FENWICK, AE
HOUGEFRYDRYCH, CSV
PINTO, IL
SMITH, DG
TAYLOR, SG
TEDDER, JM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (11) : 3028 - 3034
[7] Asymmetric synthesis of 4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans
Burgard, A
Lang, HJ
Gerlach, U
[J]. TETRAHEDRON, 1999, 55 (24) : 7555 - 7562
[8] Bronsted Acid Mediated Tandem Diels-Aider/Aromatization Reactions of Vinylindoles
Chen, Cai-Bao
Wang, Xu-Fan
Cao, Yi-Ju
Cheng, Hong-Gang
Xiao, Wen-Jing
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) : 3532 - 3535
[9] Ru-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence
Chen, Jia-Rong
Li, Chang-Feng
An, Xiao-Lei
Zhang, Ji-Ji
Zhu, Xiao-Yu
Xiao, Wen-Jing
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) : 2489 - 2492
[10] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts
Connon, Stephen J.
[J]. CHEMICAL COMMUNICATIONS, 2008, (22) : 2499 - 2510

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