Photooxygenation of chiral dienol ethers: Asymmetric synthesis of alkoxydioxines

Patrick H. Dussault, Qiang Han, Darby G. Sloss, David J. Symonsbergen

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

The addition of 1O2 to chiral dienol ethers provides a new route to alkoxydioxines (alkoxyendoperoxides). Depending upon substitution and geometry, the [4+2] cycloaddition is accompanied or even supplanted by [2+2] cycloaddition leading to alkene cleavage and/or ene-like reaction leading to allylic hydroperoxides. The diastereoselectivity of cycloaddition is ultimately limited by the conformational freedom of the dienol ether substrates.

Original languageEnglish (US)
Pages (from-to)11437-11454
Number of pages18
JournalTetrahedron
Volume55
Issue number38
DOIs
Publication statusPublished - Sep 17 1999

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Keywords

  • Cycloadditions
  • Dienes
  • Oxygen
  • Peroxides
  • Singlet

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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