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

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Ntirampebura, Deogratias [UCL] Ghosez, Léon [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 1999
Language Anglais
Journal information "Tetrahedron Letters" - Vol. 40, no. 39, p. 7079-7082 (1999)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4039
e-issn 1873-3581
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords 2-azadienes ; Diels-Alder cycloadditions ; hydroxyalkylations ; aldehydes ; 1,3-oxazinones ; beta-hydroxyamides
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Bibliographic reference Ntirampebura, Deogratias ; Ghosez, Léon. Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives. In: Tetrahedron Letters, Vol. 40, no. 39, p. 7079-7082 (1999)
Permanent URL http://hdl.handle.net/2078.1/44166