CAN-catalyzed vinylogous povarov reactions:: The first three-component synthesis of 2-functionalized tetrahydroquinolines from anilines, cinnamaldehyde and vinyl ethers

被引：21

作者：

Sridharan, Vellaisamy ^{[1
]}

Avendano, Carmen ^{[1
]}

Carlos Menendez, J. ^{[1
]}

机构：

[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

来源：

SYNLETT | 2007年 / 07期

关键词：

cycloadditions; multicomponent reactions; stereoselective; synthesis; Lewis acids; quinolines;

D O I：

10.1055/s-2007-977432

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The CAN-catalyzed reaction between anilines, cinnamaldehyde and vinyl ethers affords 2-styryl-1,2,3,4-tetrahydroquinolines. In the case of noncyclic vinyl ethers, these reactions are completely stereoselective and furnish exclusively the diastereomer with a cis relationship between the styryl and alkoxy groups.

引用

页码：1079 / 1082

页数：4

共 59 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[2] Regio- and stereo-selective aza-Diels-Alder reaction of ethyl glyoxylate 4-methoxyphenylimine with 1,3-dienes in the presence of BF3•Et2O.: Evidence for a non-concerted mechanism [J].

Alves, M. Jose ;

Azoia, Nuno G. ;

Fortes, A. Gil .

TETRAHEDRON, 2007, 63 (03) :727-734

[3]

ARALA R, 2006, SYNLETT, P1009

[4] First [4+2] cycloaddition of alkynyl Fischer carbene complexes with heterodienes. Facile synthesis of 1,4-dihydropyridines from 1-azadienes [J].

Barluenga, J ;

Tomas, M ;

LopezPelegrin, JA ;

Rubio, E .

TETRAHEDRON LETTERS, 1997, 38 (22) :3981-3984

[5]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[6]

2-A

[7] Recent developments in imino Diels-Alder reactions [J].

Buonora, P ;

Olsen, JC ;

Oh, T .

TETRAHEDRON, 2001, 57 (29) :6099-6138

[8] ANTICONVULSANT ACTIVITY OF GLYCINE-SITE NMDA ANTAGONISTS .2. TRANS 2-CARBOXY-4-SUBSTITUTED TETRAHYDROQUINOLINES [J].

CARLING, RW ;

LEESON, PD ;

MOSELEY, AM ;

SMITH, JD ;

SAYWELL, K ;

TRICKLEBANK, MD ;

KEMP, JA ;

MARSHALL, GR ;

FOSTER, AC ;

GRIMWOOD, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (01) :65-70

[9]

CELING RW, 1992, J MED CHEM, V35, P1942

[10]

CIA C, 2002, TETRAHEDRON LETT, V43, P9405

← 1 2 3 4 5 6 →