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Synthesis 1992; 1992(10): 962-965
DOI: 10.1055/s-1992-26279
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Synthesis of Some 2,5-Substituted 7-Oxabicyclo[2.2.1]heptanes: Stereochemistry of Diels-Alder Adducts of a 3-Alkylfuran

Richard L. Jarvest* , Simon A. Readshaw
  • *SmithKline Beecham Pharmaceuticals, Great Burgh, Yew Tree Bottom Road, Epsom, Surrey KT18 5XQ, England
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Publication Date:
17 September 2002 (online)

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From the Diels-Alder reaction of 3-benzylfuran with acrylonitrile were isolated three of the four possible isomeric adducts, 5(or 6)-benzyl-7-oxabicyclo [2.2.1]hept-5-ene-2-endo (or exo)-carbonitriles 6-8, with the 5-benzyl-2-endo-carbonitrile 7 predominating. The two 5-benzyl isomers, 7 and 8, were further elaborated to compounds 2-endo-aminomethyl-5-endo-benzyl-7-oxabicyclo [2.2.1]heptane hydrochloride (11) and 5-endo-benzyl-7-oxabicyclo [2.2.1]heptane-2-exo-carboxamidine hydrochloride (12).

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