Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxides

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Albrecht Berkessel and Matthias Frauenkron


Abstract

The enantiomerically pure ruthenium porphyrin 3 was synthesized in very high yield by refluxing the porphyrin 2 with Ru3(CO)12 in phenol; its subsequent use in the catalytic asymmetric epoxidation of olefins with 2,6-dichloropyridine N-oxide as terminal oxidant, to afford epoxides in good yields and with enantioselectivities up to 77%, is reported.


References

  1. G. A. Olah and A. Molnar, Hydrocarbon Chemistry, Wiley, New York, 1995 Search PubMed.
  2. E. N. Jacobsen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, New York, 1993, pp. 159–202 Search PubMed.
  3. J. P. Collman, Science, 1993, 261, 1404 CrossRef CAS.
  4. M. Hirobe, T. Higuchi and H. Ohtake, Tetrahedron Lett., 1989, 30, 6545 CrossRef CAS; M. Hirobe, T. Higuchi and H. Ohtake, J. Am. Chem. Soc., 1992, 114, 10 660 CrossRef; M. Hirobe, T. Higuchi and H. Ohtake, Heterocycles, 1995, 40, 867 CrossRef CAS.
  5. A. Berkessel and T. Schwenkreis, Tetrahedron Lett., 1993, 34, 4785 CrossRef; A. Berkessel, M. Frauenkron, T. Schwenkreis, A. Steinmetz, G. Baum and D. Fenske, J. Mol. Catal. A, 1996, 113, 321 CrossRef CAS.
  6. R. L. Halterman and S.-T. Jan, J. Org. Chem., 1991, 56, 5253 CrossRef CAS.
  7. J. W. Buchler, M. Foltz, H. Habets, J. van Kaam and K. Rohbock, Chem. Ber., 1976, 109, 1477 CAS.
  8. J. P. Collman, V. J. Lee, C. J. Kellen-Yuaen, X. Zhang, J. A. Ibers and J. I. Brauman, J. Am. Chem. Soc., 1995, 117, 692 CrossRef CAS.
  9. Z. Gross, S. Ini, M. Kapon and S. Cohen, Tetrahedron Lett., 1996, 37, 7325 CrossRef CAS.
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