Highly functionalised difluorinated cyclohexenols

P J Crowley, A.C. Moralee, Jonathan Percy, N.S. Spencer

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)1737-1740
Number of pages4
JournalSynlett
Volume2000
Issue number12
DOIs
Publication statusPublished - 2000

Keywords

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

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    Crowley, P. J., Moralee, A. C., Percy, J., & Spencer, N. S. (2000). Highly functionalised difluorinated cyclohexenols. Synlett, 2000(12), 1737-1740 . https://doi.org/10.1055/s-2000-8688