Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction: regiochemical control via the phenylsulfonyl group

Patrick J Crowley, John Fawcett, Gerry A Griffith, Andrew C Moralee, Jonathan Percy, Vittoria Salafia

Research output: Contribution to journalArticle

15 Citations (Scopus)
244 Downloads (Pure)

Abstract

A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

Original languageEnglish
Pages (from-to)3297-3310
Number of pages14
JournalOrganic and biomolecular chemistry
Issue number18
DOIs
Publication statusPublished - 2005

Keywords

  • cyclohexane polyols
  • Diels–Alder reaction
  • phenylsulfonyl group

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