Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes

Patrick H. Dussault, Tony K. Trullinger, Farhana Noor-e-Ain

Research output: Contribution to journalArticle

70 Scopus citations

Abstract

(Equation Presented) Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.

Original languageEnglish (US)
Pages (from-to)4591-4593
Number of pages3
JournalOrganic Letters
Volume4
Issue number26
DOIs
StatePublished - Dec 26 2002

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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