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Asymmetric oxidation

  • Chapter
Advanced Asymmetric Synthesis

Abstract

Of all the recent developments in asymmetric synthesis, it is the asymmetric epoxidation process1 developed in the laboratory of Professor Sharpless* that has had the greatest effect on the way organic synthesis is planned. This is because the titanium/tartrate catalyst system proved to be the first simple method to induce asymmetry that approached the goal of universal applicability and predictability. Already in this book, several examples of the Sharpless method have been discussed:

  1. 1.

    for kinetic resolution of allylic alcohols (Chapter 1);

  2. 2.

    as an example of a process in which non-linear effects are encountered (Chapter 2);

  3. 3.

    as entries to cobalt-mediated cyclisations employing the Nicholas reaction, and to iron-mediated methods of lactone synthesis (Chapter 16). In the next chapter this topic will be encountered again:

  4. 4.

    as a symmetry-splitting reaction for asymmetric induction in extended meso structures.

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References

  1. Sharpless, K.B., Woodard, S.S. and Finn, M.G., Pure Appl. Chem., 1983, 55, 1823.

    CAS  Google Scholar 

  2. Sharpless, K.B. and Michaelson, R.C., J. Am. Chem. Soc., 1973, 95, 6136.

    CAS  Google Scholar 

  3. Hanson, R.M. and Sharpless, K.B., J. Org. Chem., 1986, 51, 1922.

    CAS  Google Scholar 

  4. Jung, M.E. and Jung, Y.H., Tetrahedron Lett., 1989, 30, 6637.

    CAS  Google Scholar 

  5. Schmidt, U., Respondek, M, Lieberknecht, A., Werner, J. and Fischer, P., Synthesis, 1989, 256.

    Google Scholar 

  6. Hatakeyama, S., Numata, H., Osanai, K. and Takano, S., J. Chem. Soc, Chem. Commun., 1989, 1893.

    Google Scholar 

  7. Kitano, Y., Kusakabe, M, Kobayashi, Y. and Sato, F., J. Org. Chem., 1989, 54, 994.

    CAS  Google Scholar 

  8. Legters, J. and Zwanenburg, L.T.B., Tetrahedron Lett., 1989, 30, 4881.

    CAS  Google Scholar 

  9. Klunder, J.M., Onami, T. and Sharpless, K.B, J. Org. Chem., 1989, 54, 1295.

    CAS  Google Scholar 

  10. Mori, K. and Takeuchi, T., Lieb. Ann. Chem., 1989, 453.

    Google Scholar 

  11. Wang, Z, Tetrahedron Lett., 1989, 30, 6611.

    CAS  Google Scholar 

  12. Chaimberlin, A.R, Dezube, M, Reich, S.H. and Sail, D.J, J. Am. Chem. Soc., 1989, 111, 6247.

    Google Scholar 

  13. Rüssel, ST., Robinson, J.A. and Williams, D.J, J. Chem. Soc., Chem. Commun., 1987, 351.

    Google Scholar 

  14. Iimori, T., Still, W.C., Rheingold, A.L. and Staley, D.L., J. Am. Chem. Soc., 1989, 111, 3439.

    CAS  Google Scholar 

  15. Finn, M.G. and Sharpless, K.B, J. Am. Chem. Soc., 1991, 113, 113.

    CAS  Google Scholar 

  16. Carlier, P.R. and Sharpless, K.B., J. Org. Chem., 1989, 54, 4016.

    CAS  Google Scholar 

  17. Woodard, S.S., Finn, M.G. and Sharpless, K.B., J. Am. Chem. Soc., 1991, 113, 106.

    CAS  Google Scholar 

  18. Zhang, W., Loebach, J.L., Wilson, S.R. and Jacobsen, E.N., J. Am. Chem. Soc., 1990, 112, 2801.

    CAS  Google Scholar 

  19. Irie, R., Noda, K., Ito, Y., Matsumoto, N. and Katsuki, T, Tetrahedron Lett., 1990, 31, 7345.

    CAS  Google Scholar 

  20. Hosoya, N, Irie, R., Ito, Y. and Katsuki, T., Synlett, 1991, 691.

    Google Scholar 

  21. Hosoya, N., Hatayama, A., Irie, R., Sasaki, H. and Katsuki, T., Tetrahedron, 1994, 50, 4311.

    CAS  Google Scholar 

  22. Lee, N.H., Muci, A.R. and Jacobsen, E.N., Tetrahedron. Lett., 1991, 32, 5055 and 6533.

    CAS  Google Scholar 

  23. Yamada, T, Imagawa, K., Nagata, T. and Mukaiyama, T., Chem. Lett., 1992, 2231.

    Google Scholar 

  24. Schwenkreis, T. and Berkessel, A., Tetrahedron Lett., 1992, 34, 4785.

    Google Scholar 

  25. Irie, R, Hosoya, N. and Katsuki, T, Synlett, 1994, 255.

    Google Scholar 

  26. Irie, R., Ito, Y. and Katsuki, T., Synlett, 1991, 265.

    Google Scholar 

  27. Chang, S.B, Lee, N.H., Jacobsen, E.N., J. Org. Chem., 1993, 58, 6939; Chang, S., Galvin, J.M. and Jacobsen, E.N., J. Am. Chem. Soc,1994, 6937.

    CAS  Google Scholar 

  28. Brandes, B.D. and Jacobsen, E.N., J. Org. Chem., 1994, 59, 4378.

    CAS  Google Scholar 

  29. Brandes, B.D. and Jacobsen, E.N, Tetrahedron Lett., 1995, 36, 5123.

    CAS  Google Scholar 

  30. Sasaki, H, Irie, R, Hamada, T, Suzuki, K. and Katsuki, T, Tetrahedron, 1994, 50, 11827.

    CAS  Google Scholar 

  31. Nagata, T, Imagawa, K, Yamada, T. and Mukaiyama, T, Chem. Lett., 1994, 1259.

    Google Scholar 

  32. Nagata, T, Imagawa, K, Yamada, T. and Mukaiyama, T, Inorg. Chim. Acta, 1994, 220, 283.

    CAS  Google Scholar 

  33. Chang, S, Heid, R.M. and Jacobsen, E.N, Tetrahedron Lett., 1994, 35, 669.

    CAS  Google Scholar 

  34. Mikame, D, Hamada, T, Irie, R. and Katsuki, T, Synlett, 1995, 827.

    Google Scholar 

  35. Sasaki, H, Irie, R. and Katsuki, T, Synlett, 1994, 356.

    Google Scholar 

  36. Ewins, R.C, Henbest, H.B. and McKarbevey, M.A, J. Chem. Soc, Chem. Commun., 1967, 1085.

    Google Scholar 

  37. Davis, F.A, Harabal, M.E. and Awad, S.B, J. Am. Chem. Soc., 1983, 105, 3123.

    CAS  Google Scholar 

  38. Schurig, V, Hintzer, K, Leyrer, U, Mark, C, Pitchen, P. and Kagan, H.B, J. Organometal. Chem., 1989, 370, 81.

    CAS  Google Scholar 

  39. Coliman, J.P, Lee, V.J., Zhang, X, Ibers, J.A. and Brauman, J.I, J. Am. Chem. Soc., 1993, 115, 3834.

    Google Scholar 

  40. May, S.W., Gordon, S.L. and Steltenkamp, M.S., J. Am. Chem. Soc., 1977, 99, 2017.

    CAS  Google Scholar 

  41. May, S.W., Schwartz, R.D, Abbott, B. J. and Zaborsky, O.R, Biochem. Biophys. Acta., 1975, 403, 245.

    CAS  Google Scholar 

  42. May, S.W. and Schwartz, R.D, J. Am. Chem. Soc., 1974, 96, 4031.

    CAS  Google Scholar 

  43. White, R.F, Birnbaum, J, Meyer, R.T, ten Broeke, J, Chemerda, J.M. and Demain, A.L, Appl. Microbiol, 1971, 22, 55.

    CAS  Google Scholar 

  44. Hartmuth, CK, VanNeieuwenhze, M.S. and Sharpless, K.B, Chem. Rev., 1994, 94, 2483.

    Google Scholar 

  45. Sharpless, K.B, Teranishi, A.Y. and Backvall, J.-E, J. Am. Chem. Soc., 1997, 99, 3120; Jorgensen, K.A. and Schiot, B, Chem. Rev.,1990, 90, 1483.

    Google Scholar 

  46. Gobel, T. and Sharpless, K.B, Angew. Chem., Int. Ed. Engl., 1993, 32, 1329.

    Google Scholar 

  47. Sharpless, K.B, Amberg, W, Beller, M, Chen, H, Härtung, J, Kawanami, Y, Lubben, D, Manoury, E, Ogino, Y, Shibata, T. and Ukita, T, J. Org. Chem., 1991, 56, 4585.

    CAS  Google Scholar 

  48. Norby, P.-O, Kolb, H.C. and Sharpless, K.B, J. Am. Chem. Soc., 1994, 116, 8470.

    Google Scholar 

  49. Pearlstein, R.M, Blackburn, B.K, Davis, W.M. and Sharpless, K.B, Angew. Chem., Int. Ed. Engl., 1990, 29, 639.

    Google Scholar 

  50. Kolb, H.C, Andersson, P.G. and Sharpless, K.B, J. Am. Chem. Soc., 1994, 116, 1278.

    CAS  Google Scholar 

  51. Kolb, H.C, Bennani, Y.L. and Sharpless, K.B, Tetrahedron, Asymmetry, 1993, 4, 133; Arlington, M.P, Bennani, Y.L, Gobel, T, Walsh, P.J, Zhao, S.H. and Sharpless, K.B, Tetrahedron Lett.,1993, 34,7375.

    CAS  Google Scholar 

  52. Sharpless, K.B, Amberg, W, Bennani, Y.L, Crispino, G.A, Härtung, J, Jeong, K.-S, Kwong, H.-L, Morikawa, K, Wang, Z.-M, Xu, D. and Zhang, X.-L, J. Org. Chem., 1992, 57, 2768.

    CAS  Google Scholar 

  53. Crispino, G.A, Jeong, K.-S, Kolb, H.C, Wang, Z.-M, Xu, D. and Sharpless, K.B, J. Org. Chem., 1993, 58, 3785.

    CAS  Google Scholar 

  54. Morikawa, K, Parh, J, Andersson, P.G, Hashiyama, T. and Sharpless, K.B, J. Am. Chem. Soc., 1993, 115, 8463.

    CAS  Google Scholar 

  55. Wang, L. and Sharpless, K.B, J. Am. Chem. Soc., 1992, 114, 7566.

    Google Scholar 

  56. Xu, D, Crispino, G.A. and Sharpless, K.B, J. Am. Chem. Soc., 1992, 114, 7570.

    CAS  Google Scholar 

  57. Hang, S.-K, Park, Y.-W, Lee, D.-H, Sim, H.-S. and Jeon, J.-H, Tetrahedron, Asymmetry, 1992, 3, 705.

    Google Scholar 

  58. Rao, A.V.R., Rao, S.P. and Bhanu, M.N., J. Chem. Soc, Chem. Commun., 1992, 859.

    Google Scholar 

  59. Hirsenkorn, R., Tetrahedron Lett., 1990, 31, 7519.

    Google Scholar 

  60. Soderquist, J.A. and Rane, A.M., Tetrahedron Lett., 1993, 34, 5031.

    CAS  Google Scholar 

  61. Takano, S., Yoshimitsu, T. and Ogasawara, K., J. Org. Chem., 1994, 59, 54.

    CAS  Google Scholar 

  62. Oishi, T. and Hirama, M., Tetrahedron Lett., 1992, 33, 639.

    CAS  Google Scholar 

  63. Imada, Y., Saito, T., Kawakami, T. and Murahashi, S., Tetrahedron Lett., 1992, 33, 5081.

    CAS  Google Scholar 

  64. Hanessian, S., Meffre, P., Girard, M., Beaudoin, S., Sanceau, J.-Y. and Bennani, Y.L., J. Org. Chem., 1993, 58, 1991.

    CAS  Google Scholar 

  65. Tomioka, K., Nakajima, M. and Koga, K, J. Am. Chem. Soc., 1987, 109, 6213.

    CAS  Google Scholar 

  66. Hentges, S.G. and Sharpless, K.B., J. Am. Chem. Soc., 1980, 102, 4263.

    CAS  Google Scholar 

  67. Palucki, M, Hanson, P. and Jackobsen, E.N., Tetrahedron Lett., 1993, 33, 5055.

    Google Scholar 

  68. Noda, K., Hosoya, N., Irie, R., Yamashita, Y. and Katsuki, T., Tetrahedron, 1994, 50, 9609.

    CAS  Google Scholar 

  69. Nakajima, K., Kojima, M. and Fujita, J., Chem. Lett., 1986, 1483; Nakajima, K., Kojima, M. and Fujita, J., Bull. Chim. Soc. Jap.,1991, 64, 1318.

    Google Scholar 

  70. Kosatsu, N., Nishibayashi, Y., Sugita, T. and Uemura, S., Tetrahedron Lett., 1992, 33, 5319.

    Google Scholar 

  71. Samuel, O., Ronan, B. and Kagan, H.B., J. Organometal. Chem., 1989, 370, 43.

    CAS  Google Scholar 

  72. Di Furia, F., Licini, G. and Modena, G., Gazz. Chim. Ital., 1990, 120, 165.

    Google Scholar 

  73. Samuel, O., Ronan, B. and Kagan, H.B, J. Organometal. Chem., 1989, 370, 43.

    CAS  Google Scholar 

  74. Denney, D.B., Napier, R. and Cammarata, A., J. Org. Chem., 1963, 30, 3151; Muzart, J., J. Mol. Catal,1991, 64, 381.

    Google Scholar 

  75. Rispens, M.T., Zondervan, C. and Feringa, B.L., Tetrahedron, Asymmetry, 1994, 6, 661.

    Google Scholar 

  76. Andrus, M.B., Argade, A.B., Chen, X. and Pamment, M.G., Tetrahedron Lett., 1995, 36, 2945.

    CAS  Google Scholar 

  77. Discordia, R.P., Murphy, CK. and Dittmer, D.C., Tetrahedron Lett., 1990, 31, 5603.

    CAS  Google Scholar 

  78. Grennberg, H., Gogoll, A. and Backvall, J.-E., J. Org. Chem., 1991, 56, 5808.

    CAS  Google Scholar 

  79. Holland, H.L., Carter, I.M., Chenchaiah, P.C., Khan, S.H., Munoz, B, Ninniss, R.W. and Richards, D., Tetrahedron Lett., 1985, 26, 6409.

    CAS  Google Scholar 

  80. Crabb, T.A. and Soilleux, S.L., J. Chem. Soc, Perkin Trans. 1, 1985, 1381.

    Google Scholar 

  81. Battersby, A.R., Sheldrake, P.W., Staunton, J. and Williams, D.C., J. Chem. Soc, Perkin Trans. 1, 1976, 1056.

    Google Scholar 

  82. Phillips, G.T., Matcham, G.W.J., Bertola, M.A., Marx, A.F. and Koger, H.S., Eur. Pat. Appl, EP 20521517, Dec. 1986.

    Google Scholar 

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Stephenson, G.R. (1996). Asymmetric oxidation. In: Stephenson, G.R. (eds) Advanced Asymmetric Synthesis. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0797-9_17

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  • DOI: https://doi.org/10.1007/978-94-007-0797-9_17

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