Towards novel difluorinated sugar mimetics; syntheses and conformational analyses of highly-functionalised difluorinated cyclooctenones
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Colleges, School and Institutes
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.
|Number of pages||12|
|Journal||Organic and Biomolecular Chemistry|
|Publication status||Published - 1 Jan 2005|