Palladium-catalysed asymmetric allylic substitution: synthesis of α- and β-amino acids

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Justin F. Bower, Roshan Jumnah, Andrew C. Williams and Jonathan M. J. Williams


Abstract

Methodology has been established for the formation of enantiomerically enriched α-amino acids using palladium-catalysed allylic amination. The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity. Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives. Additionally, enantiomerically enriched β-amino acids have been prepared in high enantiomeric excess. Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.


References

  1. (a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 1989, 28, 1173 CrossRef; (b) S. Silvana, D. Sinou, M. Perez, M. Moreno-Manas, R. Pleixants and M. Villaroya, Tetrahedron Lett., 1994, 34, 7085; (c) W. Carruthers and R. C. Moses, J. Chem. Soc., Perkin Trans. 1, 1988, 2255 RSC.
  2. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura and Y. J. Kazunori, J. Am. Chem. Soc., 1989, 111, 6301 CrossRef CAS.
  3. P. B. Auburn, P. B. Mackenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033 CrossRef CAS.
  4. B. M. Trost and R. C. Bunt, J. Am. Chem. Soc., 1994, 116, 4089 CrossRef CAS.
  5. Y. Tanigawa, K. Nishimura, A. Kawasaki and S. I. Murahashi, Tetrahedron Lett., 1982, 23, 5549 CrossRef CAS.
  6. S. Byström, R. Aslanian and J. E. Bäckvall, Tetrahedron Lett., 1985, 26, 1749 CrossRef.
  7. Y. Inoue, M. Taguchi, M. Toyofuku and H. Hashimoto, Bull. Chem. Soc. Jpn., 1984, 57, 3021 CAS.
  8. R. D. Connell, T. Rein, B. Åkermark and P. Helquist, J. Org. Chem., 1988, 53, 3845 CrossRef CAS.
  9. For other reports of nitrogen nucleophiles in palladium-catalysed allylic substitution see; (a) C. G. Frost, J. Howarth and J. M. J. Williams, Tetrahedron: Asymmetry, 1992, 3, 1089 CrossRef CAS; (b) A. Merzouk and F. Guibé, Tetrahedron Lett., 1992, 33, 477 CrossRef CAS; (c) M. Takagi and K. Yamamoto, Chem. Lett., 1989, 2123 CAS; (d) H. H. Baer and Z. S. Hanna, Can. J. Chem., 1981, 59, 889 CAS; (e) T. Tsuda, Y. Horii, Y. Nakagawa, T. Ishida and T. Saegusa, J. Org. Chem., 1989, 54, 977 CrossRef CAS; (f) H. Kunz, Angew. Chem., Int. Ed. Engl., 1988, 27, 1375 CrossRef; (g) D. R. Deardorff, R. G. II Linde, A. M. Martin and M. J. Shulman, J. Org. Chem., 1989, 54, 2759 CrossRef CAS; (h) F. Liotta, R. Unelius, J. Kojak and T. Norin, Acta Chem. Scand., 1992, 46, 686 CAS; (i) M. Safi and D. Sinou, Tetrahedron Lett., 1991, 32, 2025 CrossRef CAS.
  10. (a) J. A. Marshall, A. W. Garofalo and R. C. Sedrani, Synlett, 1992, 643 CAS; (b) J. A. Marshall and A. W. Garofalo, J. Org. Chem., 1993, 58, 3675 CrossRef CAS.
  11. T. Rosen, I. M. Lico and D. T. W. Chu, J. Org. Chem., 1988, 53, 1580 CrossRef.
  12. R. Jumnah, A. C. Williams and J. M. J. Williams, Tetrahedron Lett., 1994, 34, 6619 CrossRef CAS.
  13. P. H. J. Carlsen, T. Katsuki, V. S. Martin and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936 CrossRef CAS.
  14. (a) G. J. Dawson, C. G. Frost, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149 CrossRef CAS; (b) J. Sprinz and G. Helmchen, Tetrahedron Lett., 1993, 34, 1769 CrossRef CAS; (c) P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566 CrossRef.
  15. J. V. Allen, S. J. Coote, G. J. Dawson, C. G. Frost, C. J. Martin and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1994, 2065 RSC.
  16. P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573 CrossRef CAS.
  17. R. Jumnah, A. C. Williams and J. M. J. Williams, Synlett, 1995, 821 CrossRef CAS.
  18. J. O. Osby, M. G. Martin and B. Ganem, Tetrahedron Lett., 1984, 25, 2093 CrossRef CAS.
  19. T. Inaba, I. Kozono, M. Fujita and K. Ogura, Bull. Chem. Soc. Jpn., 1992, 2359 CAS.
  20. M. T. Nunez and V. S. Martin, J. Org. Chem., 1990, 55, 1928 CrossRef CAS.
  21. (a) P. R. Auburn, P. B. MacKenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033 CrossRef CAS; (b) P. B. MacKenzie, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2046 CrossRef CAS; (c) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683 CrossRef CAS; (d) J. M. Brown, D. I. Hulmes and P. J. Guiry, Tetrahedron, 1994, 50, 4493 CrossRef CAS.
  22. (a) G. J. Dawson, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1995, 36, 461 CrossRef CAS; (b) G. J. Dawson, J. M. J. Williams and S. J. Coote, Tetrahedron: Asymmetry, 1995, 6, 2535 CrossRef CAS.
  23. (a) A. P. Krapcho, Synthesis, 1982, 805, 893 CrossRef; (b) P. von Matt, G. C. Lloyd-Jones, A. B. E. Minidis, A. Pfaltz, L. Macko, M. Neuberger, M. Zehnder, H. Reugger and P. S. Pregosin, Helv. Chim. Acta, 1995, 78, 265 CrossRef.
  24. (a) T. Shioiri, K. Ninomiya and S. Yamada, J. Am. Chem. Soc., 1972, 94, 6203 CrossRef CAS; (b) P. E. Eaton and B. K. Ravi Shankar, J. Org. Chem., 1984, 49, 185 CrossRef CAS.
  25. S. Murahashi, T. Taniguchi, Y. Imada and Y. Tanigawa, J. Org. Chem., 1989, 54, 3292 CrossRef CAS.
  26. C. Briguet, C. Freppel, J. Richer and M. Zador, Can. J. Chem., 1974, 52, 3201 CAS.
  27. K. Balenovic and N. Bregant, Tetrahedron, 1959, 5, 44 CrossRef CAS.
  28. A. A. D'Souza, M. Mortevalli, A. J. Robinson and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1995, 1 RSC.
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