Catalysis Letters

, Volume 4, Issue 2, pp 163–167 | Cite as

Regioselective epoxidation by air of sterol esters bearing several double bonds using a ruthenium porphyrin catalyst

  • Manuella Tavares
  • René Ramasseul
  • Jean-Claude Marchon
Article

Abstract

A series of sterol esters bearing varying patterns of unsaturation on the nucleus, side chain, and acyl substituent were epoxidized using trans-dioxoruthenium(VI) tetramesitylporphyrin as catalyst and air as source of oxygen. Attack at the steroid nucleus is generally favored, and a high degree of β-stereoselectivity is obtained except for conjugated 5,7 diene systems which yield a ca. 1∶1 mixture of 5,6α and 5,6β epoxides.

Keywords

Oxygen Ester Physical Chemistry Steroid Catalysis 

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References and notes

  1. [1]
    J.C. Marchon and R. Ramasseul, J. Chem. Soc. Chem. Commun. (1988) 298.Google Scholar
  2. [2]
    J.C. Marchon and R. Ramasseul, J. Mol. Catal. 51 (1989) 29.Google Scholar
  3. [3]
    J.T. Groves and R. Quinn, J. Am. Chem. Soc. 107 (1985) 5790.Google Scholar
  4. [4]
    J.T. Groves and K.H. Ahn, Inorg. Chem. 26 (1987) 3833.Google Scholar
  5. [5]
    N. Rajapakse, B.R. James and D. Dolphin, Catal. Lett. 2 (1989) 219.Google Scholar
  6. [6]
    J.C. Marchon and R. Ramasseul, Synthesis (Stuttgart) (1989) 389.Google Scholar
  7. [7]
    D.P. Michaud, N.T. Nashed and D.M. Jerina, J. Org. Chem. 50 (1985) 1835.Google Scholar
  8. [8]
    B. Loeken-Shewsbury and M. Gut, U.S. Patent 3 468 875 (1969).Google Scholar
  9. [9]
    J.T. Groves and R. Neumann, J. Am. Chem. Soc. 111 (1989) 2900.Google Scholar
  10. [10]
    R.B. Boar, D.A. Lewis and J.F. McGhie, J. Chem. Soc. Perkin Trans. I (1972) 2231.Google Scholar

Copyright information

© J.C. Baltzer A.G. Scientific Publishing Company 1990

Authors and Affiliations

  • Manuella Tavares
    • 1
  • René Ramasseul
    • 1
  • Jean-Claude Marchon
    • 1
  1. 1.Laboratoire de Chimie/Chimie de Coordination (URA 1194 du CNRS), Départment de Recherche FondamentaleCentre d'Etudes Nucléaires de GrenobleGrenobleFrance

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