Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives

被引：41

作者：

Ntirampebura, D ^{[1
]}

Ghosez, L ^{[1
]}

机构：

[1] Univ Catholique Louvain, Lab Chim Organ Synth, B-1348 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 39期

关键词：

2-azadienes; Diels-Alder cycloadditions; hydroxyalkylations; aldehydes; 1,3-oxazinones; beta-hydroxyamides;

D O I：

10.1016/S0040-4039(99)01444-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aza-1,3-dienes 1 which are readily prepared from carboxylic acids cycloadd to aldehydes to give good yields of 1,3-oxazinones 3. The cycloadditions were highly diastereoselective in favour of the endo adducts. Hydrolysis of 1,3-oxazinones 3 stereoselectively yielded the corresponding beta-hydroxyamides 4. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：7079 / 7082

页数：4

共 9 条

[1] PREPARATION AND REACTIVITY OF 2-AZA-1,3-BUTADIENES - A DIELS-ALDER ROUTE TO 5,6-DIHYDRO-2H-1,3-OXAZINE DERIVATIVES [J].

BARLUENGA, J ;

JOGLAR, J ;

FUSTERO, S ;

GOTOR, V ;

KRUGER, C ;

ROMAO, MJ .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (09) :3652-3663

[2] A REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPERIDONES [J].

BAYARD, P ;

GHOSEZ, L .

TETRAHEDRON LETTERS, 1988, 29 (47) :6115-6118

[3] 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

[4] A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy [J].

Ghosez, L ;

Jnoff, E ;

Bayard, P ;

Sainte, F ;

Beaudegnies, R .

TETRAHEDRON, 1999, 55 (11) :3387-3400

[5] Electrophilic amination of 2-azadienes [J].

Gouverneur, V ;

Ghosez, L .

TETRAHEDRON, 1996, 52 (21) :7585-7598

[6] ASYMMETRIC AMINATION OF CARBOXYLIC-ACIDS VIA A DIELS-ALDER STRATEGY [J].

GOUVERNEUR, V ;

GHOSEZ, L .

TETRAHEDRON LETTERS, 1991, 32 (39) :5349-5352

[7] 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

[8] Solution phase library of perhydrooxazin-4-ones. [J].

Panunzio, M ;

Villa, M ;

Missio, A ;

Rossi, T ;

Seneci, P .

TETRAHEDRON LETTERS, 1998, 39 (36) :6585-6588

[9] Diels-Alder reactions of 2-azabutadienes with aldehydes: Ab initio and density functional theoretical study of the reaction mechanism, regioselectivity, acid catalysis, and stereoselectivity [J].

Venturini, A ;

Joglar, J ;

Fustero, S ;

Gonzalez, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3919-3926

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