Intramolecular reactions of hydroperoxides and oxetanes: Stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes

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Abstract

(Chemical Equation Presented) The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecifically to furnish 1,2-dioxolanes. The corresponding 6-exo cyclizations are slower and proceed with moderate stereoselectivity. In the case of hydroperoxy acetals, 5-exo nucleophilic transfer of alkoxide competes effectively with 6-exo attack by the hydroperoxide.

Original languageEnglish (US)
Pages (from-to)4333-4335
Number of pages3
JournalOrganic Letters
Volume7
Issue number20
DOIs
StatePublished - Sep 29 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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