Skip to main content
SpringerLink
Log in

Palladium allyl π-complexes in asymmetric synthesis

  • Chapter
Advanced Asymmetric Synthesis

Abstract

This chapter discusses the use of palladium-catalysed allylic substitution in enantioselective and diastereoselective processes. The early sections will outline the mechanism and scope of the reaction, as well as the behaviour and properties of the π-allylpalladium intermediates. Based on recent results, it seems likely that future advances in the asymmetric version of the palladiumcatalysed allylic substitution reaction will be made through an understanding of the intermediates involved in the catalytic cycle. There are several reviews covering the scope of this reaction in a general sense.1

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Godleski, S.A., in Comprehensive Organic Synthesis, Vol. 4, Trost, B.M. (ed.), Pergamon Press, Oxford, 1991, p. 585; (b) Consiglio, G. and Waymouth, R.M., Chem. Rev.,1989, 89, 257; (c) Tsuji, J., Pure Appl. Chem.,1986, 58,869; (c) Frost, CG., Howarth, J. and Williams, J.M.J., Tetrahedron: Asymmetry,1992, 3, 1089.

    Chapter  Google Scholar 

  2. Rieke, R.D., Kavaliunas, A.V., Rhyne, L.D. and Fraser, D.J.J., J. Am. Chem. Soc., 1979, 101, 246.

    Article  CAS  Google Scholar 

  3. Robinson, S.D. and Shaw, B.L., J. Chem. Soc., 1963, 4806.

    Google Scholar 

  4. Trost, B.M. and Metzher, P.J., J. Am. Chem. Soc., 1980, 102, 3572.

    Article  CAS  Google Scholar 

  5. Mason, R. and Whimp, P.O., J. Chem. Soc. (A), 1969, 2709; (b) Smith, A.E., Acta Cryst.,1965, 18,331; (c) Hegedus, L.S., Åkermark, ?., Olsen, D.J, Anderson, O.P. and Zetterberg, ?, J. Am. Chem. Soc,1982, 104,697.

    Google Scholar 

  6. Pregosin, P.S., Rueggcr, H, Salzmann, R, Albinati, A, Lianza, F. and Kunz, R.W, Organometallics, 1994, 13, 83.

    Article  CAS  Google Scholar 

  7. Norrby, P.-O, Åkermark, B, Haeffner, F., Hansson, S. and Blomberg, M, J. Am. Chem. Soc., 1993, 115, 4859.

    Article  CAS  Google Scholar 

  8. Tsuji, J., Takashashi, H. and Morikawa, M, Tetrahedron Lett., 1965, 4387.

    Google Scholar 

  9. Atkins, K.E., Walker, W.E. and Manyik, R.M, Tetrahedron Lett., 1970, 3821.

    Google Scholar 

  10. Trost, B.M. and Verhoeven, T.R., J. Am. Chem. Soc., 1978, 100, 3435.

    Article  CAS  Google Scholar 

  11. Tsuji, J. and Yamakawa, T, Tetrahedron Lett., 1976, 613.

    Google Scholar 

  12. Tsuji, J, Shimizu, I., Minami, I, Ohashi, Y, Takahashi, K. and Sugiura, T, J. Org. Chem., 1985, 50, 1523.

    Article  CAS  Google Scholar 

  13. Stary, I, Stara, I.G. and Kocovsky, P, Tetrahedron Lett., 1993, 34, 179.

    Article  CAS  Google Scholar 

  14. Trost, B.M. and Warner, R.W., J. Am. Chem. Soc., 1982, 104, 6112.

    Article  CAS  Google Scholar 

  15. Tanigawa, Y, Nishimura, K, Kawasaki, A. and Murahashi, S, Tetrahedron Lett., 1982, 23, 5549.

    Article  CAS  Google Scholar 

  16. Trost, B.M, Schmuff, N.R. and Miller, M.J, J. Am. Chem. Soc., 1980, 102, 5979.

    Article  CAS  Google Scholar 

  17. Tsuji, Y, Yamada, N. and Tanaka, S, J. Org. Chem., 1993, 58, 16.

    Article  CAS  Google Scholar 

  18. Murahashi, S, Tanigawa, Y, Imada, Y. and Taniguchi, Y, Tetrahedron Lett., 1986, 27, 227.

    Article  CAS  Google Scholar 

  19. Baer, H.H. and Hanna, Z.S, Can. J. Chem., 1981, 59, 889.

    Article  CAS  Google Scholar 

  20. Byström, S.E, Aslanian, R. and Bäckvall, J.E, Tetrahedron Lett., 1985, 26, 1749.

    Article  Google Scholar 

  21. Takagi, M. and Yamamoto, K, Chem. Lett., 1989, 2123; (b) Inoue, Y, Taguchi, M, Toyofuku, M. and Hashimoto, H, Bull. Chem. Soc. Jpn,1984, 57,3021.

    Google Scholar 

  22. Inoue, Y, Taguchi, M, Toyofuku, M. and Hashimoto, H, Bull. Chem. Soc. Jpn., 1984, 57, 3021; (b) Connell, R.D, Rein, T, Äkermark, ?. and Helquist, P, J. Org. Chem., 1988, 53, 3845.

    Article  CAS  Google Scholar 

  23. Mandai, T, Matsumoto, T. and Tsuji, J, Synlett, 1993, 113.

    Google Scholar 

  24. Greenspoon, N. and Keinan, E, J. Org. Chem., 1988, 53, 3723.

    Article  CAS  Google Scholar 

  25. Tsuji, J, Sakai, K, Nagashima, H. and Shimizu, I, Tetrahedron Lett., 1981, 22, 131; (b) Larock, R.C, Harrison, L.W. and Hsu, M.H, J. Org. Chem.,1984, 49, 3662.

    Article  CAS  Google Scholar 

  26. Julia, M, Nei, M. and Saussime, L, J. Organomet. Chem., 1979, 181, C17.

    Article  CAS  Google Scholar 

  27. Äkermark, B, Nystrom, J.E, Rein, T, Bläckvall, J.E, Helquist, P. and Aslanian, R, Tetrahedron Lett., 1984, 25, 5719.

    Article  Google Scholar 

  28. Trost, B.M, Yashida, J. and Lautens, M, J. Am. Chem. Soc., 1983, 105, 4494; (b) Tsuji, Y, Kajita, S, Isobe, S. and Funato, M, J. Org. Chem.,1993, 58,3607.

    Article  CAS  Google Scholar 

  29. Coulson, D.R, Inorg. Synth., 1972, 13, 21; (b) Coulson, D.R., Inorg. Synth., 1990, 28,107.

    Article  Google Scholar 

  30. Bläckvall, J.-E, Nyström, J.-E. and Nordberg, R.E, J. Am. Chem. Soc., 1985, 107, 3676.

    Article  Google Scholar 

  31. Ukai, T, Kawazura, H, Ishii, Y, Bonnet, J.J. and Ibers, J.A, J. Organomet. Chem., 1914 65, 253.

    Article  Google Scholar 

  32. Tatsuno, Y, Yoshida, T. and Otsuka, S, Inorg. Synth., 1990, 28, 342.

    Article  CAS  Google Scholar 

  33. Mandai, T, Matsumoto, T, Tsuji, J. and Saito, S, Tetrahedron Lett., 1993, 34, 2513.

    Article  CAS  Google Scholar 

  34. Takemoto, T., Nishikimi, Y, Sodeoka, M. and Shibasaki, M., Tetrahedron Lett, 1992, 33, 3527.

    Article  CAS  Google Scholar 

  35. Yamamoto, T., Akimoto, M., Saito, O. and Yamamoto, A., Organometallics, 1986, 5, 1559; (b) Kurosawa, H., J. Organomet. Chem.,1987, 334,243.

    Article  CAS  Google Scholar 

  36. Åkermark, B., Hansson, S, Krakenberger, B., Vitagliano, A. and Zetterberg, K., Organometallics, 1984, 3, 679.

    Article  Google Scholar 

  37. Trost, B.M., Angew. Chem., Int. Ed. Engl., 1989, 28, 1173.

    Article  Google Scholar 

  38. Fiaud, J.-C. and Legros, J.-Y., J. Org. Chem., 1987, 52, 1907.

    Article  CAS  Google Scholar 

  39. Trost, B.M. and Verhoeven, T.R., J. Org. Chem., 1976, 41, 3215.

    Article  CAS  Google Scholar 

  40. Matsushita, H. and Negishi, E., J. Chem. Soc, Chem. Commun., 1982, 160.

    Google Scholar 

  41. Deardorff, D.R., Linde, R.G., Martin, A.M. and Shulman, M.J, J. Org. Chem., 1989, 54, 2759.

    Article  CAS  Google Scholar 

  42. Kang, S.-K, Kim, S.-G. and Lee, J.-S, Tetrahedron: Asymmetry, 1992, 3, 1139.

    Article  CAS  Google Scholar 

  43. Corradini, P, Maglio, G, Musco, A. and Paiaro, G, J. Chem. Soc, Chem. Commun., 1966, 618.

    Google Scholar 

  44. Trost, B.M, Verhoeven, T.R. and Fortunak, J.M., Tetrahedron Lett., 1979, 2301.

    Google Scholar 

  45. Hayashi, T, Yamamoto, A. and Hagihara, T, J. Org. Chem., 1986, 51, 723.

    Article  CAS  Google Scholar 

  46. Yamamoto, K, Deguchi, R, Ogimura, Y. and Tsuji, J, Chem. Lett., 1984, 1657.

    Google Scholar 

  47. Genet, J.P, Kopola, N, Juge, S, Ruiz-Montes, J, Antunes, O.A.C. and Tanier, S, Tetrahedron Lett., 1990, 31, 3133.

    Article  CAS  Google Scholar 

  48. Hiroi, K, Abe, J, Suga, K, Sato, S. and Koyama, T, J. Org. Chem., 1994, 59, 203.

    Article  CAS  Google Scholar 

  49. Marshall, J.A, Andrews, R.C. and Lebioda, L, J. Org. Chem., 1987, 52, 2378.

    Article  CAS  Google Scholar 

  50. Trost, B.M. and Lee, P.H, J. Am. Chem. Soc., 1991, 113, 5076.

    Article  CAS  Google Scholar 

  51. Baldwin, I.C. and Williams, J.M.J, unpublished results.

    Google Scholar 

  52. Nilsson, Y.I.M, Andersson, P.G. and Bäckvall, J.-E, J. Am. Chem. Soc., 1993, 115, 6609.

    Article  CAS  Google Scholar 

  53. Yamaguchi, M, Shima, T, Yamagishi, T. and Hida, M, Tetrahedron Lett., 1990, 31, 5049.

    Article  CAS  Google Scholar 

  54. Trost, B.M. and Murphy, D.J, Organometallics, 1985, 4, 1143.

    Article  CAS  Google Scholar 

  55. Hayashi, T, Yamamoto, A, Hagihara, T. and Ito, Y, Tetrahedron Lett., 1986, 27, 191; (b) Hayashi, T, Pure and Appl. Chem.,1988, 60, 7.

    Article  CAS  Google Scholar 

  56. Okada, Y, Minami, T, Sasaki, Y, Umezu, Y. and Yamaguchi, M, Tetrahedron Lett., 1990, 31, 3905; (b) Okada, Y, Minami, T, Umezu, Y, Nishikawa, S, Mori, R. and Nakayama, Y, Tetrahedron: Asymmetry,1991, 2, 667.

    Article  CAS  Google Scholar 

  57. Yamazaki, A, Morimoto, T. and Achiwa, K, Tetrahedron: Asymmetry, 1993, 4, 2287.

    Article  CAS  Google Scholar 

  58. Leutenegger, V, Umbricht, G, Fahrni, C, von Matt, P. and Pfaltz, A, Tetrahedron, 1992, 48, 2143.

    Article  CAS  Google Scholar 

  59. Pfaltz, A, Ace. Chem. Res., 1993, 26, 339.

    Article  CAS  Google Scholar 

  60. Togni, A, Tetrahedron: Asymmetry, 1991, 2, 683; (b) Togni, A, Rihs, G, Pregosin, P.S. and Ammann, C, Helv. Chim. Acta,1990, 73,723.

    Article  CAS  Google Scholar 

  61. Kubota, H, Nakajima, M. and Koga, K, Tetrahedron Lett., 1993, 34, 8135.

    Article  CAS  Google Scholar 

  62. Sprinz, J. and Helmchen, G, Tetrahedron Lett., 1993, 34, 1769; (b) von Matt, P. and Pfaltz, A, Angew. Chem., Int. Ed. Engl,1993, 32, 566; (c) Dawson, G.J, Frost, CG, Williams, J.M. J. and Coote, S.J, Tetrahedron Lett.,1993, 34,3149; (d) Brown, J.M, Hulmes, D.I. and Guiry, P.J, Tetrahedron,in press.

    Article  CAS  Google Scholar 

  63. Åkermark, B, Krakenberger, B, Hansson, S. and Vitagliano, A, Organometallics, 1987, 6, 620.

    Article  Google Scholar 

  64. Sprinz, J, Kiefer, M, Helmchen, G, Reggelin, M, Huttner, G, Walter, O. and Zsolnai, L, Tetrahedron Lett., 1994, 35, 1523.

    Article  CAS  Google Scholar 

  65. Reiser, O, Angew. Chem., Int. Ed. Engl., 1993, 32, 547.

    Article  Google Scholar 

  66. Frost, C.G. and Williams, J.M.J, Tetrahedron Lett., 1993, 34, 2015; (b) Frost, C.G. and Williams, J.M.J, Tetrahedron: Asymmetry,1993, 4, 1785; (c) Dawson, G.J, Frost, C.G, Martin, C.J., Williams, J.M.J, and Coote, S.J, Tetrahedron Lett.,1993, 34,7793.

    Article  CAS  Google Scholar 

  67. Allen, J.V. and Williams, J.M.J, manuscript in preparation.

    Google Scholar 

  68. Frost, C.G. and Williams, J.M.J, manuscript in preparation.

    Google Scholar 

  69. Hayashi, T, Iwamura, H, Naito, M, Matsumoto, Y, Uozumi, Y, Miki, M. and Yanagi, K, J. Am. Chem. Soc., 1994, 116, 775.

    Article  CAS  Google Scholar 

  70. Mackenzie, P.B, Whelan, J. and Bosnich, B, J. Am. Chem. Soc., 1985, 107, 2046; (b) Farrar, D.H. and Payne, N.C, J. Am. Chem. Soc,1985, 107,2054.

    Article  CAS  Google Scholar 

  71. Trost, B.M. and van Vranken, D.L, Angew. Chem., Int. Ed. Engl., 1992, 31, 228.

    Article  Google Scholar 

  72. Fiaud, J.C, DeGournay, A.H., Lachevéque, M. and Kagan, H.B., J. Organomet. Chem., 1978, 154, 175; (b) Hayashi, T, Kanechira, K, Tsuchiya, H. and Kumada, M, J. Chem. Soc, Chem. Commun., 1982, 1162; (c) Hayashi, T, Kanehira, K, Hagihara, T. and Kumada, M, J. Org. Chem.,1988, 53,113; (d) Sawamura, M, Nagata, H, Sakamoto, H. and Ito, Y, J. Am. Chem. Soc,1992, 114,2586.

    Article  CAS  Google Scholar 

Download references

Authors
  1. J. M. J. Williams
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. School of Chemical Sciences, University of East Anglia, Norwich, UK

    G. R. Stephenson

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Williams, J.M.J. (1996). Palladium allyl π-complexes in asymmetric synthesis. In: Stephenson, G.R. (eds) Advanced Asymmetric Synthesis. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0797-9_15

Download citation

  • DOI: https://doi.org/10.1007/978-94-007-0797-9_15

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-3731-0

  • Online ISBN: 978-94-007-0797-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation