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Synthesis 2002(14): 2043-2052
DOI: 10.1055/s-2002-34367
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
Further Information
Received
15 July 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
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
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