SYNTHESIS AND DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF HALOGENATED 2-AZA 1,3-DIENES

被引：19

作者：

BARLUENGA, J

GONZALEZ, FJ

FUSTERO, S

GARCIAGRANDA, S

PEREZCARRENO, E

机构：

[1] UNIV VALENCIA,FAC FARM,E-46010 VALENCIA,SPAIN

[2] UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33071 OVIEDO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of mono- and trihalogenated derivatives of 2-aza 1,3-dienes 2 and 3 is described. The first example of diastereofacial selectivity in Diels-Alder reactions of heterodienes of type 2 with electron-poor dienophiles is reported, and a model for the explanation of the observed epimeric ratios, based on the interactions between diene and dienophile, is proposed.

引用

页码：4459 / 4463

页数：5

共 21 条

[1] AN EXCEPTIONALLY SIMPLE AND UNEXPECTED ONE-POT SYNTHESIS OF NEW 4,6-DIAZASEMIBULLVALENES
BARLUENGA, J
GONZALEZ, FJ
FUSTERO, S
SOLANS, X
DOMENECH, MV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (15) : 1057 - 1059
[2] UNACTIVATED 2-AZA-1,3-DIENES - HALOGENATION AND FACE SELECTIVITY IN DIELS-ALDER REACTIONS
BARLUENGA, J
GONZALEZ, FJ
FUSTERO, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 397 - 398
[3] BARLUENGA J, 1989, J CHEM RES-S, P66
[4] PREPARATION AND REACTIVITY OF 2-AZA-1,3-BUTADIENES - A DIELS-ALDER ROUTE TO 5,6-DIHYDRO-2H-1,3-OXAZINE DERIVATIVES
BARLUENGA, J
JOGLAR, J
FUSTERO, S
GOTOR, V
KRUGER, C
ROMAO, MJ
[J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (09): : 3652 - 3663
[5] BARLUENGA J, 1990, SYNLETT, P129
[6] BENSON, 1973, ORG SYNTH, V5, P663
[7] PI-FACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF C-2-VINYL GLYCALS - STEREOCONTROLLED ROUTE TO ANNULATED C-GLYCOPYRANOSIDES
BURNOUF, C
LOPEZ, JC
COLVOFLORES, FG
LABORDE, MD
OLESKER, A
LUKACS, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (11) : 823 - 825
[8] De Kimpe N., 1988, CHEM ALPHA HALOKETON
[9] 1,4-DEHYDROCHLORINATION OF ALPHA-CHLOROIMINES AS A SUITABLE PROCEDURE FOR THE SYNTHESIS OF UNACTIVATED 2-AZA-1,3-DIENES AND 3-AZA-1,3,5-TRIENES
DEKIMPE, N
YAO, ZP
BOEYKENS, M
NAGY, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (19) : 2771 - 2774
[10] REACTIVITY OF BETA-HALOENAMINES - A REVIEW
DEKIMPE, N
SCHAMP, N
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (1-2) : 71 - 135

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