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

60 Citations (Scopus)

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

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Hydrogen Peroxide
Stereoselectivity
Lewis Acids
Antimalarials
hydrogen peroxide
acids
oxetane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides : Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes. / Dussault, Patrick H.; Trullinger, Tony K.; Noor-e-Ain, Farhana.

In: Organic Letters, Vol. 4, No. 26, 26.12.2002, p. 4591-4593.

Research output: Contribution to journalArticle

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