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

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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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.

Item type: Article
ID code: 10080
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: 15 Apr 2015 08:38
URI: http://strathprints.strath.ac.uk/id/eprint/10080

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