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Synlett 2000; 2000(12): 1737-1740
DOI: 10.1055/s-2000-8688
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Highly Functionalised Difluorinated Cyclohexenols

Patrick J. Crowley* , Andrew C. Moralee, Jonathan M. Percy, Neil S. Spencer
  • *Zeneca Agrochemicals, Jealott's Hill Research Station, Bracknell, Berkshire, RG42 6ET, UK; Fax +44 121 414 4403; E-mail: jmpercy@chemistry.bham.ac.uk
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Publication Date:
31 December 2000 (online)

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Alkenoate 5 prepared on a multigramme scale from trifluoroethanol underwent cycloaddition with furan in good yield. Reduction of the ester group in the endo-cycloadduct 7a with DIBAl-H also resulted in decarbamoylation to reveal a diol which was protected as an acetonide 10. Various methods for nucleophilic ring opening were explored releasing highly functionalised difluorinated cyclohexenols, and suggesting a novel route to difluorinated analogues of cyclitols and monosaccharides.

difluoroalkenoate - fluorinated dienophile - Stille - Diels-Alder - ring opening