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Synlett 2000; 2000(5): 0713-0715
DOI: 10.1055/s-2000-6591
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Lewis Acid Catalyzed Hetero Diels-Alder Reactions of Olefinic and Acetylenic Compounds with 6-Methyl-3,5-dichloro-2H-1,4-oxazin-2-one

Wim De Borggraeve* , Frederik Rombouts, Erik Van der Eycken, Georges J. Hoornaert
  • *Laboratorium voor Organische Synthese, Department of Chemistry, K. U. Leuven, Celestijnenlaan 200F, B-3001 Heverlee, Belgium; Fax + 32(0)16 32 79 90; E-mail: Georges.Hoornaert@chem.kuleuven.ac.be
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Publication Date:
31 December 2000 (online)

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For the first time Lewis acid catalysis is described for the hetero Diels-Alder reaction of a conformationally fixed 2-azadiene system in a 2H-1,4-oxazin-2-one with a variety of alkenes and alkynes. The reaction is shown to occur under much milder conditions as hitherto reported. With dienophiles containing no heteroatoms an important increase in regio- and/or stereoselectivity is observed.

Diels-Alder reactions - catalysis - heterocycles - regioselectivity - stereoselectivity

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