Towards novel difluorinated sugar mimetrics; syntheses and conformational analyses of highly-functionalised difluorinated cyclooctenones

J.M. Percy, G.A. Griffith, S. Pintat, C.A. Smith, N. Spencer, E. Uneyama

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Abstract

Highly-functionalised difluorinated cyclooctenones were synthesised from trifluoroethanol using either metallated difluoroenol acetal or carbamate chemistry, followed by a [2,3]-Wittig rearrangement or aldol reaction. Efficient RCM reactions afforded the title compounds which showed rather restricted fluxional behaviour by VT 19F NMR. Topological characterisation by molecular modelling and NOESY/ROESY experiments offered a number of challenges, but allowed the identification of two favoured boat-chair conformers which interconverted by pseudorotation with relatively large activation barriers.
Original languageEnglish
Pages (from-to)2701-2712
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume3
DOIs
Publication statusPublished - 2005

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Keywords

  • difluorinated cyclooctenones
  • difluorinated sugar mimetics

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