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Synthesis 2002(14): 2043-2052
DOI: 10.1055/s-2002-34367
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective β-Hydroxyalkylation and β-Hydroxycarboxylation of Amides­ by a Diels-Alder Strategy

Deogratias Ntirampeburaa, Léon Ghosez*a,b
a Department of Chemistry, Catholic University of Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)472944; e-Mail: ghosez@chim.ucl.ac.be;
b European Institute of Chemistry and Biology (IECB), c/o ENSCPB, Avenue Pey Berland 16, 33607 Pessac, France
Fax: +33(5)57962222; e-Mail: l.ghosez@iecb-polytechnique.u-bordeaux.fr;
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Publication History

Received 15 July 2002
Publication Date:
26 September 2002 (online)

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Abstract

Acid chlorides readily condensed with N-silylated imines in the presence of a base to generate 2-azadienes. These underwent Diels-Alder cycloadditions with a wide variety of aldehydes. In most cases the cycloadditions were diastereoselective in favor of the 3,4-cis-oxazinone adducts. Ethanolysis stereoselectively yielded products of hydroxyalkylation or hydroxycarboxylation of the primary amides derived from the initial acid chlorides.

Key words

amides - azadienes - heterocycles - oxazinones - aldehydes - Diels-Alder reactions