Stereoselective dioxygenation of enoates

Patrick H Dussault, Kevin R. Woller, Michael C. Hillier

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The auxiliary-directed reaction of singlet oxygen with tiglate esters furnishes an asymmetric synthesis of 3-hydroperoxy-2-methylidene butenoates. Although previous reports have suggested that s-cis enoate conformers undergo preferential oxygenation relative to the s-trans conformers, our results suggest that both conformers are reactive and that the modest stereoselectivity is based upon a conformational equilibrium favoring the s-trans conformer.

Original languageEnglish (US)
Pages (from-to)8929-8940
Number of pages12
JournalTetrahedron
Volume50
Issue number30
DOIs
StatePublished - Jan 1 1994

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Stereoselectivity
Singlet Oxygen
Oxygenation
Esters

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereoselective dioxygenation of enoates. / Dussault, Patrick H; R. Woller, Kevin; C. Hillier, Michael.

In: Tetrahedron, Vol. 50, No. 30, 01.01.1994, p. 8929-8940.

Research output: Contribution to journalArticle

Dussault, PH, R. Woller, K & C. Hillier, M 1994, 'Stereoselective dioxygenation of enoates', Tetrahedron, vol. 50, no. 30, pp. 8929-8940. https://doi.org/10.1016/S0040-4020(01)85363-1
Dussault, Patrick H ; R. Woller, Kevin ; C. Hillier, Michael. / Stereoselective dioxygenation of enoates. In: Tetrahedron. 1994 ; Vol. 50, No. 30. pp. 8929-8940.
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