Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions

John Fawcett, Gerry A Griffith, Jonathan Percy, Emi Uneyama

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Topologically mobile difluorinated cyclooctenones undergo rapid, high-yielding, and completely stereoselective epoxidations with methyl-(trifluoromethyl)dioxirane. The epoxides resist conventional hydrolysis but react smoothly in basic media under microwave irradiation to afford unique hemiacetals and hemiaminals in good yield.
Original languageEnglish
Pages (from-to)1277-1280
Number of pages4
JournalOrganic Letters
Volume6
Issue number8
DOIs
Publication statusPublished - 2004

Keywords

  • difluorinated cyclooctenones
  • stereoselective epoxidations
  • methyl(trifluoromethyl)dioxirane
  • hydrolysis

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