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Synlett 1991; 1991(5): 353-355
DOI: 10.1055/s-1991-34726
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The Effect of Lewis Acids on the Intramolecular Diels-Alder Reaction of the Furan Diene

Christine Rogers* , Brian A. Keay
  • *Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada
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Publication Date:
07 March 2002 (online)

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Lewis acids have been found to accelerate the intramolecular Diels-Alder reaction of the furan diene in which the diene and dienophile are connected by four-carbon atoms [2-(4-oxo-5-alkenyl)furans]. The methodology has been extended to include acetylenic dienophiles [2-(1,1-dimethyl-4-oxo-5-alkynyl)furans], which cyclize to give the oxatricyclo ring system (5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2H-2,4a-epoxynaphthalene).