First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex

被引：149

作者：

Sundararajan, G ^{[1
]}

Prabagaran, N

Varghese, B

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

[2] Indian Inst Technol, Reg Sophisticated Instrumentat Ctr, Madras 600036, Tamil Nadu, India

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 13期

关键词：

D O I：

10.1021/ol0159221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(matrix presented) R1, R2 = (-OCH2CH2-), (-OCH2CH2CH2-), (-CH=CH-CH2-), (-OCH2CH3, H) (R,R)-3-Aza-3-benzyl-1,5-dihydroxy-1,5-diphenylpentane (1) ligated Ti(IV) complex (1-TiCl2) is used as a chiral Lewis acid catalyst for promoting asymmetric IED Diels-Alder reaction between electron-rich dienophiles and electron-poor dienes. Here we introduce a facile route for the synthesis of asymmetric tetrahydroquinoline derivatives using the above-mentioned chiral catalyst reagent in the presence of 4 Å molecular sieves. The reactions proceed with moderate yields and at times high enantioselectivty.

引用

页码：1973 / 1976

页数：4

共 33 条

[1]

ALVARADO PL, 1997, J CHEM SOC P1, P229

[2] Indium trichloride (InCl3)catalyzed imino Diels-Alder reactions:: An efficient synthesis of cyclopentaquinolines, azabicyclooctanones and azabicyclononanones. [J].

Babu, G ;

Perumal, PT .

TETRAHEDRON, 1998, 54 (08) :1627-1638

[3] Resolution of the flumequine intermediate 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline [J].

Bálint, J ;

Egri, G ;

Vass, G ;

Schindler, J ;

Gajáry, A ;

Friesz, A ;

Fogassy, E .

TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :809-813

[4]

Beller M, 2000, CHEM-EUR J, V6, P2513, DOI 10.1002/1521-3765(20000717)6:14<2513::AID-CHEM2513>3.0.CO

[5]

2-V

[6] DIELS-ALDER REACTIONS OF AZADIENES [J].

BOGER, DL .

TETRAHEDRON, 1983, 39 (18) :2869-2939

[7] DIASTEREOFACIAL SELECTIVITY IN THE CYCLOADDITION OF CHIRAL GLYOXYLATE IMINES TO CYCLOPENTADIENE AND INDENE - SYNTHESIS OF OPTICALLY-ACTIVE TETRAHYDROQUINOLINES [J].

BORRIONE, E ;

PRATO, M ;

SCORRANO, G ;

STIVANELLO, M ;

LUCCHINI, V ;

VALLE, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2245-2250

[8] SCHIZOID REACTIVITY OF N-BENZYLIDENE ANILINE TOWARD CLAY-CATALYZED CYCLO-ADDITIONS [J].

CABRAL, J ;

LASZLO, P ;

MONTAUFIER, MT .

TETRAHEDRON LETTERS, 1988, 29 (05) :547-550

[9] MECHANISTIC ASPECTS OF THE BORON-TRIFLUORIDE CATALYZED, INTERMOLECULAR DIELS-ALDER CYCLOADDITION OF AN UNACTIVATED 2-AZA 1,3-DIENE WITH ELECTRON-DONATING-SUBSTITUTED DIENOPHILES [J].

CHENG, YS ;

HO, E ;

MARIANO, PS ;

AMMON, HL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5678-5686

[10] Some reactions of ammonia and primary amines with propanol, 2-chloroethanol, 2,2-dichloroethanol and 2,2,2-trichloroethanol in acetonitrile [J].

Crampton, MR ;

Lord, SD ;

Millar, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (05) :909-914

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