Reaction of 1O2 with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides

P. H. Dussault, U. R. Zope

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

Original languageEnglish (US)
Pages (from-to)2187-2190
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number13
DOIs
StatePublished - Mar 27 1995

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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