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 Citations (Scopus)

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
StatePublished - Sep 17 1999

Fingerprint

Ethers
Cycloaddition
Cycloaddition Reaction
Alkenes
Ether
Hydrogen Peroxide
Substitution reactions
Geometry
Substrates

Keywords

  • Cycloadditions
  • Dienes
  • Oxygen
  • Peroxides
  • Singlet

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Photooxygenation of chiral dienol ethers : Asymmetric synthesis of alkoxydioxines. / Dussault, Patrick H; Han, Qiang; Sloss, Darby G.; Symonsbergen, David J.

In: Tetrahedron, Vol. 55, No. 38, 17.09.1999, p. 11437-11454.

Research output: Contribution to journalArticle

Dussault, Patrick H ; Han, Qiang ; Sloss, Darby G. ; Symonsbergen, David J. / Photooxygenation of chiral dienol ethers : Asymmetric synthesis of alkoxydioxines. In: Tetrahedron. 1999 ; Vol. 55, No. 38. pp. 11437-11454.
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