Competitive fine-tuning of heteroaromatic imines as dienophiles or dienes in the Lewis acid-mediated Diels-Alder reaction with cyclopentadiene

被引：13

作者：

Loh, TP ^{[1
]}

Koh, KSV ^{[1
]}

Sim, KY ^{[1
]}

Leong, WK ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 48期

关键词：

aza Diels-Alder; imine; azadiene;

D O I：

10.1016/S0040-4039(99)01770-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heteroaromatic imines function as dienophiles or dienes in the Lewis acid-mediated Diels-Alder reaction with cyclopentadiene depending on the substituent on the imine. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8447 / 8451

页数：5

共 14 条

[1]

[Anonymous], 1991, Comprehensive Organic Synthesis

[2] ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION [J].

BAILEY, PD ;

BROWN, GR ;

KORBER, F ;

REED, A ;

WILSON, RD .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1263-1282

[3] Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]heptanes [J].

Chen, ZM ;

Trudell, ML .

CHEMICAL REVIEWS, 1996, 96 (03) :1179-1193

[4] STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE [J].

COREY, EJ ;

LOH, TP ;

ACHYUTHARAO, S ;

DALEY, DC ;

SARSHAR, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5600-5602

[5] 2-AZA-1,3-DIENES - METHODS OF SYNTHESIS AND STEREOCHEMICAL STUDIES [J].

GHOSEZ, L ;

BAYARD, P ;

NSHIMYUMUKIZA, P ;

GOUVERNEUR, V ;

SAINTE, F ;

BEAUDEGNIES, R ;

RIVERA, H ;

FRISQUEHESBAIN, AM ;

WYNANTS, C .

TETRAHEDRON, 1995, 51 (40) :11021-11042

[6] ASYMMETRIC AZA-DIELS-ALDER REACTION - ENANTIOSELECTIVE AND DIASTEREOSELECTIVE REACTION OF IMINE MEDIATED BY CHIRAL LEWIS ACID [J].

HATTORI, K ;

YAMAMOTO, H .

TETRAHEDRON, 1993, 49 (09) :1749-1760

[7] TOTAL SYNTHESIS OF (+/-)-ISOPROSOPININE-B AND (+/-)-DESOXOPROSOPININE [J].

HOLMES, AB ;

THOMPSON, J ;

BAXTER, AJG ;

DIXON, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (01) :37-39

[8]

HOLMES AB, 1992, J CHEM SOC CHEM COMM, P787

[9] Asymmetric Diels-Alder reactions of 2-azadienes catalyzed by a chiral copper(II) complex. A general route to enantiomerically pure piperidones [J].

Jnoff, E ;

Ghosez, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2617-2618

[10]

KOBAYASHI S, 1995, SYNTHESIS-STUTTGART, P1195

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