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

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 9, 1997, Pages 1411-1420

  Bower, Justin F ^a   Jumnah, Roshan ^a   Williams, Andrew C ^b   Williams, Jonathan M J ^a,c  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

^c UNIVERSITY OF BATH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010315056     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a606586d     Document Type: Article

References (47)

1. (a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 1989, 28, 1173;
2. (b) S. Silvana, D. Sinou, M. Perez, M. Moreno-Manas, R. Pleixants and M. Villaroya, Tetrahedron Lett., 1994, 34, 7085;
3. (c) W. Carruthers and R. C. Moses, J. Chem. Soc., Perkin Trans. 1, 1988, 2255.
4. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Miura and Y. J. Kazunori, J. Am. Chem. Soc., 1989, 111, 6301.
5. P. B. Auburn, P. B. Mackenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033.
6. B. M. Trost and R. C. Bunt, J. Am. Chem. Soc., 1994, 116, 4089.
7. Y. Tanigawa, K. Nishimura, A. Kawasaki and S. I. Murahashi, Tetrahedron Lett., 1982, 23, 5549.
8. S. Byström, R. Aslanian and J. E. Bäckvall, Tetrahedron Lett., 1985, 26, 1749.
9. Y. Inoue, M. Taguchi, M. Toyofuku and H. Hashimoto, Bull. Chem. Soc. Jpn., 1984, 57, 3021.
10. R. D. Connell, T. Rein, B. Akermark and P. Helquist, J. Org. Chem., 1988, 53, 3845.
11. 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;
12. (b) A. Merzouk and F. Guibe, Tetrahedron Lett., 1992, 33, 477;
13. (c) M. Takagi and K. Yamamoto, Chem. Lett., 1989, 2123;
14. (d) H. H. Baer and Z. S. Hanna, Can. J. Chem., 1981, 59, 889;
15. (e) T. Tsuda, Y. Horii, Y. Nakagawa, T. Ishida and T. Saegusa, J. Org. Chem., 1989, 54, 977;
16. (f) H. Kunz, Angew. Chem., Int. Ed. Engl., 1988, 27, 1375;
17. (g) D. R. Deardorff, R. G. II Linde, A. M. Martin and M. J. Shulman, J. Org. Chem., 1989, 54, 2759;
18. (h) F. Liotta, R. Unelius, J. Kojak and T. Norin, Acta Chem. Scand., 1992, 46, 686;
19. (i) M. Safi and D. Sinou, Tetrahedron Lett., 1991, 32, 2025.
20. (a) J. A. Marshall, A. W. Garofalo and R. C. Sedrani, Synlett, 1992, 643;
21. (b) J. A. Marshall and A. W. Garofalo, J. Org. Chem., 1993, 58, 3675.
22. T. Rosen, I. M. Lico and D. T. W. Chu, J. Org. Chem., 1988, 53, 1580.
23. R. Jumnah, A. C. Williams and J. M. J. Williams, Tetrahedron Lett., 1994, 34, 6619.
24. P. H. J. Carlsen, T. Katsuki, V. S. Martin and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936.
25. (a) G. J. Dawson, C. G. Frost, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1993, 34, 3149;
26. (b) J. Sprinz and G. Helmchen, Tetrahedron Lett., 1993, 34, 1769;
27. (c) P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566.
28. 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.
29. P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573.
30. R. Jumnah, A. C. Williams and J. M. J. Williams, Synlett, 1995, 821.
31. J. O. Osby, M. G. Martin and B. Ganem, Tetrahedron Lett., 1984, 25, 2093.
32. T. Inaba, I. Kozono, M. Fujita and K. Ogura, Bull. Chem. Soc. Jpn., 1992, 2359.
33. M. T. Nunez and V. S. Martin, J. Org. Chem., 1990, 55, 1928.
34. (a) P. R. Auburn, P. B. MacKenzie and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033;
35. (b) P. B. MacKenzie, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2046;
36. (c) A. Togni, Tetrahedron: Asymmetry, 1991, 2, 683;
37. (d) J. M. Brown, D. I. Hulmes and P. J. Guiry, Tetrahedron, 1994, 50, 4493.
38. (a) G. J. Dawson, J. M. J. Williams and S. J. Coote, Tetrahedron Lett., 1995, 36, 461;
39. (b) G. J. Dawson, J. M. J. Williams and S. J. Coote, Tetrahedron: Asymmetry, 1995, 6, 2535.
40. (a) A. P. Krapcho, Synthesis, 1982, 805, 893;
41. (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.
42. (a) T. Shioiri, K. Ninomiya and S. Yamada, J. Am. Chem. Soc., 1972, 94, 6203;
43. (b) P. E. Eaton and B. K. Ravi Shankar, J. Org. Chem., 1984, 49, 185.
44. S. Murahashi, T. Taniguchi, Y. Imada and Y. Tanigawa, J. Org. Chem., 1989, 54, 3292.
45. C. Briguet, C. Freppel, J. Richer and M. Zador, Can. J. Chem., 1974, 52, 3201.
46. K. Balenovic and N. Bregant, Tetrahedron, 1959, 5, 44.
47. A. A. D'Souza, M. Mortevalli, A. J. Robinson and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1995, 1.