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.
Original language | English |
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Pages (from-to) | 2701-2712 |
Number of pages | 12 |
Journal | Organic and Biomolecular Chemistry |
Volume | 3 |
DOIs | |
Publication status | Published - 2005 |
Keywords
- difluorinated cyclooctenones
- difluorinated sugar mimetics