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Oxidation of Silyl Enol Ethers

  • William P. Weber
Part of the Reactivity and Structure Concepts in Organic Chemistry book series (REACTIVITY, volume 14)

Abstract

A number of useful synthetic transformations are based on the selective oxidation of the electron rich C-C double bond of trimethylsilyl enol ethers.

Keywords

Palladium Acetate Enol Ether Methyl Morpholine Silyl Enol Ether Ketene Acetal 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Ryu, I., Murai, S., Hatayama, Y., Sonoda, N.: Tetrahedron Lett. 3455 (1978)Google Scholar
  2. 2.
    Fleming, I., Paterson, I.: Syn. 736 (1979)Google Scholar
  3. 3.
    Jung, M.E., Pan, Y.G., Rathke, M.W., Sullivan, D.F., Woodbury, R.P.: J. Org. Chem. 42, 3961 (1977)CrossRefGoogle Scholar
  4. 4.
    Jung, M.E.: J. Org. Chem. 41, 1479 (1976)CrossRefGoogle Scholar
  5. 5.
    Jung, M.E., Speltz, L.M.: J. Am. Chem. Soc. 98, 7882 (1976)CrossRefGoogle Scholar
  6. 6.
    Ito, Y., Hirao, H., Saegusa, T.: J. Org. Chem. 43, 1011 (1978)CrossRefGoogle Scholar
  7. 7.
    Ojima, I., Nihonyanagi, N., Kogure, T., Kumagai, M., Horiuchi, S., Nakatsugawa, N., Nagai, Y.: J. Organometal. Chem. 94, 449 (1975)CrossRefGoogle Scholar
  8. 8.
    Ito, Y., Konoike, T., Saegusa, T.: J. Am. Chem. Soc. 97, 649 (1975)CrossRefGoogle Scholar
  9. 9.
    Rubottom, G.M., Gruber, J.M., Kincaid, K.: Syn. Commun. 6, 59 (1976)CrossRefGoogle Scholar
  10. 10.
    Rubottom, G.M., Gruber, J.M., Mong, G.M.: J. Org. Chem. 41, 1673 (1976)CrossRefGoogle Scholar
  11. 11.
    Asaoka, M., Yanagida, N., Sugimura, N., Takei, H.: Bull. Chem. Soc. Japan, 53, 1061 (1980)CrossRefGoogle Scholar
  12. 12.
    Rubottom, G.M., Vazquez, M.A., Pelegrina, D.R.: Tetrahedron Lett. 4319 (1974)Google Scholar
  13. 13.
    Brook, A.G., MacRae, D.M.: J. Organometal. Chem. 77, C19 (1974)CrossRefGoogle Scholar
  14. 14.
    Hassner, A., Reuss, R.H., Pinnick, H.W.: J. Org. Chem. 40, 3427 (1975)CrossRefGoogle Scholar
  15. 15.
    Rubottom, G.M., Gruber, J.M.: J. Org. Chem. 43, 1599 (1978)CrossRefGoogle Scholar
  16. 16.
    Rubottom, G.M., Marrero, R., I. Org. Chem. 40, 3783 (1975)CrossRefGoogle Scholar
  17. 17.
    Rubottom, G.M., Gruber, J.M., Boeckman, Jr.R.K., Ramaiah, M., Medwid, J.B., Tetrahedron Lett. 4603 (1978)Google Scholar
  18. 18.
    Clark, R.D., Heathcock, C.H.: Tetrahedron Lett. 1713 (1974)Google Scholar
  19. 19.
    Clark, R.D., Heathcock, C.H.: Tetrahedron Lett. 2027 (1974)Google Scholar
  20. 20.
    Clark, R.D., Heathcock, C.H.: J. Org. Chem. 41, 1396 (1976)CrossRefGoogle Scholar
  21. 21.
    Rubottom, G.M., Nieves, M.I.L.: Tetrahedron Lett. 2423 (1972)Google Scholar
  22. 22.
    Friedrich, E., Lutz, W.: Angew. Chem. Int. Ed. 16, 413 (1977)Google Scholar
  23. 23.
    Jefford, C.W., Rimbault, C.G.: Tetrahedron Lett. 2375 (1977)Google Scholar
  24. 24.
    Kuo, Y.N., Chen, F., Ainsworth, C., Bloomfield, J.J.: J. Chem. Sec. D, 135 (1971)Google Scholar
  25. 25.
    Adam, W., Liu, J.C.: J. Am. Chem. Soc. 94, 2894 (1972)CrossRefGoogle Scholar
  26. 26.
    Adam, W., Steinmetzer, H.C.: Angew. Chem. Int. Ed. 11, 540 (1972)CrossRefGoogle Scholar
  27. 27.
    Adam, W., Alzérreca, A., Liu, J.C., Yany, F.: J. Am. Chem. Soc. 99, 5768 (1977)CrossRefGoogle Scholar
  28. 28.
    Rubottom, G.M., Mott, R.C., Juve, Jr., H.D.: J. Org. Chem. 46, 2717 (1981)CrossRefGoogle Scholar
  29. 29.
    Van Rheenan, Kelly, R.C., Cha, D.Y.: Tetrahedron Lett. 1973 (1976)Google Scholar
  30. 30.
    McCormick, J.P., Tomasik, W., Johnson, M.W.: Tetrahedron Lett. 607 (1981)Google Scholar
  31. 31.
    Kaneda, K., Kii, N., Jitsukawa, K., Teranishi, S.: Tetrahedron Lett. 2595 (1981)Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1983

Authors and Affiliations

  • William P. Weber
    • 1
  1. 1.Department of ChemistryUniversity of Southern CaliforniaUniversity Park, Los AngelesUSA

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