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Synlett 1990; 1990(2): 93-94
DOI: 10.1055/s-1990-20997
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Synthesis and Coupling Reactions of 2-Substituted 3-Oxepanones

Martin J. Davies* , Christopher J. Moody, Roger J. Taylor
  • *Department of Chemistry, Imperial College of Science, Technology & Medicine, London SW7 2AY, England
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Publication Date:
08 March 2002 (online)

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A range of 2-substituted 3-oxepanones 3 (7 examples) is prepared from 2-tetrahydropyranones (δ-lactones) via rhodium(II) acetate catalysed cyclisation of intermediate diazo alcohols. The 2-benzenesulphonyl-7-hexyl-3-oxepanone (3e) and the corresponding 2-diethoxyphosphoryl derivative 3f are versatile substrates for further elaboration and are readily converted into 2-substituted 7-hexyl-3-triethylsiloxyoxepanes 5 and 2-alkylidene-7-hexyl-3-oxepanones 6.