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Silicon Reagents for Organic Synthesis pp 243–254Cite as

Cycloaddition and Electrocyclic Reactions of Silyl Enol Ethers

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Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 14))

Abstract

The electron rich double bonds of silyl enol ethers and silyloxy dienes undergo a variety of cycloaddition and electrocyclic reactions.

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References

  1. Krepski, L.R., Hassner, A.: J. Org. Chem. 43, 3173 (1978)

    Article  CAS  Google Scholar 

  2. Brady, W.T., Lloyd, R.M.: J. Org. Chem. 44, 2560 (1979)

    Article  CAS  Google Scholar 

  3. Brady, W.T., Lloyd, R.M.: J. Org. Chem. 45, 2025 (1980)

    Article  CAS  Google Scholar 

  4. Brady, W.T., Lloyd, R.M.: J. Org. Chem. 46, 1322 (1981)

    Article  CAS  Google Scholar 

  5. Mizuno, K., Okamoto, H., Pac, C., Sakurai, H., Murai, S., Sonoda, N.: Chem. Lett. 237 (1975)

    Google Scholar 

  6. Akhtar, I.A., McCullough, J.J.: J. Org. Chem. 46, 1447 (1981)

    Article  CAS  Google Scholar 

  7. Clark, R.D., Untch, K.G.: J. Org. Chem. 44, 253 (1979)

    Article  CAS  Google Scholar 

  8. Cunico, R.F.: J. Organometal. Chem. 212, C51 (1981)

    Article  CAS  Google Scholar 

  9. Ibuka, I., Ito, Y., Mori, Y., Anoyama, T., Inubushi, Y.: Syn. Comm. 7, 131 (1977)

    Article  CAS  Google Scholar 

  10. Hengge, E., Pletka, H.D.: Monat. für Chem. 104, 1071 (1973)

    Article  CAS  Google Scholar 

  11. Jung, M.E., McCombs, C.A.: Tetrahedron Lett. 2935 (1976)

    Google Scholar 

  12. Simchen, G., Kober, W.: Synthesis, 259 (1976)

    Google Scholar 

  13. Wunderly, S.W., Weber, W.P.: J. Org. Chem. 43, 2277 (1978)

    Article  CAS  Google Scholar 

  14. Danishefsky, S., Kitahara, T.: J. Am. Chem. Soc. 96, 7807 (1974)

    Article  CAS  Google Scholar 

  15. Danishefsky, S., Kitahara, T.: J. Org. Chem. 40, 538 (1975)

    Article  CAS  Google Scholar 

  16. Danishefsky, S., Singh, R.K., Harayama, T.: J. Am. Chem. Soc. 99, 5810 (1977)

    Article  CAS  Google Scholar 

  17. Danishefsky, S., Harayama, T., Singh, R.K.: J. Am. Chem. Soc. 101, 7008 (1979)

    Article  CAS  Google Scholar 

  18. Danishefsky, S., Yan, C.F., McCurry, Jr., P.M.: J. Org. Chem. 42, 1819 (1977)

    Article  CAS  Google Scholar 

  19. Danishefsky, S., Walker, F.J.: J. Am. Chem. Soc. 101, 7018 (1979)

    Article  CAS  Google Scholar 

  20. Danishefsky, S., Singh, R.K., Gammill, R.B.: J. Org. Chem. 43, 379 (1978)

    Article  CAS  Google Scholar 

  21. Danishefsky, S., Yan, C.F., Singh, R.K., Gammill, R.B., McCurry, Jr., P.M., Fritsch, N., Clardy, J.: J. Am. Chem. Soc. 101, 7001 (1979)

    Article  CAS  Google Scholar 

  22. Snowden, R.L.: Tetrahedron Lett. 97 (1981)

    Google Scholar 

  23. Snowden, R.L.: Tetrahedron Lett. 101 (1981)

    Google Scholar 

  24. Bloch, R.: Tetrahedron Lett. 3945 (1979)

    Google Scholar 

  25. Ardecky, R.J., Kerdesky, F.A.J., Cava, M.P.: J. Org. Chem. 46, 1483 (1981)

    Article  CAS  Google Scholar 

  26. Asaoka, M., Miyake, K., Takei, H.: Chem. Lett. 167 (1977)

    Google Scholar 

  27. Brownbridge, P., Chan, T.H.: Tetrahedron Lett. 3423 (1980)

    Google Scholar 

  28. Giguere, R.J., Hoffmann, H.M.R., Hursthouse, M.B., Trotter, J.: J. Org. Chem. 46, 2868 (1981)

    Article  CAS  Google Scholar 

  29. Ireland, R.E., Mueller, R.H., Willard, A.K.: J. Am. Chem. Soc. 98, 2868 (1976)

    Article  CAS  Google Scholar 

  30. Ireland, R.E., Mueller, R.H.: J. Am. Chem. Soc. 94, 5897 (1972)

    Article  CAS  Google Scholar 

  31. Katzenellenbogen, J.A., Christy, K.J.: J. Org. Chem. 39, 3315 (1974)

    Article  CAS  Google Scholar 

  32. Bloomfield, J.J.: Tetrahedron Lett. 587 (1968)

    Google Scholar 

  33. Coates, R.M., Sandefur, L.O., Smillie, R.D.: J. Am. Chem. Soc. 97, 1619 (1975)

    Article  CAS  Google Scholar 

  34. Bloch, R., Boivin, F., Bortolussi, M.: J. Chem. Soc. Chem. Commun. 371 (1976)

    Google Scholar 

  35. Bloch, R., Denis, J.M.: J. Organometal. Chem. 90, C9 (1975)

    Article  CAS  Google Scholar 

  36. Thies, R.W., Bolesta, R.W.: J. Org. Chem. 41, 1233 (1976)

    Article  CAS  Google Scholar 

  37. Thies, R.W.: J. Am. Chem. Soc. 94, 7074 (1972)

    Article  CAS  Google Scholar 

  38. Thies, R.W., Wills, M.T., Chin, A.W., Schick, L.E., Walton, E.S.: J. Am. Chem. Soc. 95, 5281 (1973)

    Article  CAS  Google Scholar 

  39. Thies, R.W., Billigmeier, J.E.: J. Am. Chem. Soc. 96, 200 (1974)

    Article  CAS  Google Scholar 

  40. Thies, R.W.: J. Chem. Soc. Chem. Commun. 237 (1971)

    Google Scholar 

  41. Pak, C., Okamoto, H., Sakurai, H.: Synthesis, 589 (1978)

    Google Scholar 

  42. Sakurai, H., Shirahata, A., Hosomi, A.: Angew. Chem. Int. Ed. 18, 163 (1979)

    Article  Google Scholar 

  43. Shimizu, N., Tsuno, Y.: Chem. Lett. 103 (1979)

    Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, University of Southern California, 90007, University Park, Los Angeles, CA, USA

    William P. Weber

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  1. William P. Weber
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© 1983 Springer-Verlag Berlin Heidelberg

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Weber, W.P. (1983). Cycloaddition and Electrocyclic Reactions of Silyl Enol Ethers. In: Silicon Reagents for Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68661-0_15

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  • DOI: https://doi.org/10.1007/978-3-642-68661-0_15

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68663-4

  • Online ISBN: 978-3-642-68661-0

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