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

Research output: Contribution to journalArticle

37 Citations (Scopus)

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

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Dioxanes
Dioxolanes
acetals
alkoxides
Hydrogen Peroxide
attack
Stereoselectivity
Acetals
Cyclization
synthesis
oxetane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Intramolecular reactions of hydroperoxides and oxetanes : Stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes. / Dai, Peng; Dussault, Patrick H.

In: Organic Letters, Vol. 7, No. 20, 29.09.2005, p. 4333-4335.

Research output: Contribution to journalArticle

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