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

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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. (https://doi.org/10.1039/B505978J)

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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.

ORCID iDs

Percy, J.M. ORCID logoORCID: https://orcid.org/0000-0001-8636-2704, Griffith, G.A., Pintat, S., Smith, C.A., Spencer, N. and Uneyama, E.;
CORE (COnnecting REpositories)