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

Authors
Ntirampebura, D Ghosez, L
Citation
D. Ntirampebura et L. Ghosez, Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives, TETRAHEDR L, 40(39), 1999, pp. 7079-7082
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
39
Year of publication
1999
Pages
7079 - 7082
Database
ISI
SICI code
0040-4039(19990924)40:39<7079:CO2TAA>2.0.ZU;2-P
Abstract
2-Aza-1,3-dienes 1 which are readily prepared from carboxylic acids cycload d 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-hydroxya mides 4. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.