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

Research output: Contribution to journalArticle

Authors

  • GA Griffith
  • S Pintat
  • CA Smith
  • Neil Spencer
  • E Uneyama

Colleges, School and Institutes

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 F-19 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.

Details

Original languageEnglish
Pages (from-to)2701-2712
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number15
Publication statusPublished - 1 Jan 2005