Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes

Patrick J Crowley, John Fawcett, Benson M Kariuki, Andrew C Moralee, Jonathan Percy, Vittoria Salafia

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.
Original languageEnglish
Pages (from-to)4125-4128
Number of pages4
JournalOrganic Letters
Volume4
Issue number23
DOIs
Publication statusPublished - 2002

Keywords

  • strain relief
  • monofluoroalkene
  • ring opening

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