Percy, J.M. and Griffith, G.A. and Pintat, S. and Smith, C.A. and Spencer, N. and Uneyama, E. (2005) Towards novel difluorinated sugar mimetrics; syntheses and conformational analyses of highly-functionalised difluorinated cyclooctenones. Organic and Biomolecular Chemistry, 3. pp. 2701-2712.
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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.
|Keywords:||difluorinated cyclooctenones , difluorinated sugar mimetics, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Strathprints Administrator|
|Date Deposited:||13 Jul 2011 08:30|
|Last modified:||07 Jan 2017 00:20|