Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton: Application of the Staudinger reaction to chiral imines of methyl glyoxylate

Tetrahedron

Volumn 54, Issue 38, 1998, Pages 11501-11516

  Barreau, Michel ^a   Commerçon, Alain ^a   Mignani, Serge ^a   Mouysset, Dominique ^b   Perfetti, Patricia ^b   Stella, Lucien ^b  

^a SANOFI   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; BETA LACTAM; ETHYLAMINE; GLYOXYLIC ACID DERIVATIVE; IMINE; KETENE DERIVATIVE; METHYLGLYOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032541591     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00683-8     Document Type: Article

References (70)

1. 1. (a) Marshall, G. R.; Gorin, F. A.; Moore, M. L. Ann. Rep. Med. Chem. 1978, 13, 227-238.
2. (b) Fauchère, J. L. QSAR in Drug Design and Toxicology D. Hadzi and B. Jerman-Blazic Eds.; Amsterdam, 1987, 221.
3. (c) Hruby, V. J. Trends Pharmacol. Sci. 1987, 8, 336.
4. 2. (a) Spatola, A. F. in Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B., Ed.; Marcel Dekker, 1983; Vol. 7, p 267-357.
5. (b) Farmer, P. S. in Drug Design; Ariens, E. J., Ed.; Academic Presss: New York, 1981; Vol. 10, p 119-143.
6. (c) Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720.
7. (d) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1-19.
8. (e) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
9. (f) Goodman, M.; Zhang, J. Chemtracts-Organic Chemistry 1997, 10, 629-645.
10. (g) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron, 1997, 53, 12789-12854.
11. 3. (a) Hirschmann, R.; Sprengeler, P. A.; Kawasaki, T.; Leahy, J. W.; Shakespeare, W. C.; Smith, A. B., III. J. Am. Chem. Soc. 1992, 114, 9699-9701.
12. (b) Tourwe, D.; Verschueren, K.; Van Binst, G.; Davis, P.; Porrece, F.; Hruby, V. J. Bioorg. Med. Chem. Lett. 1992, 2, 1305-1308.
13. (c) Bolos, J.; Perez, A.; Gilbert, S.; Anglada, L.; Sacristan, A.; Ortiz, J. A. J. Org. Chem. 1992, 57, 3535-3539.
14. 4. (a) Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooks, J. R.; Saperstein, R. Science, 1980, 210, 656-658.
15. (b) Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 47, 104-109.
16. (c) Freidinger, R. M. J. Org. Chem. 1985, 50, 3631-3633.
17. 5. (a) Ward, P.; Ewan, G. B.; Jordan, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848-1851.
18. (b) Olson, G. L.; Voss, M. E.; Hill; D. E.; Kahn, M.; Madison, V. S.; Cook, C. M. J. Am. Chem. Soc, 1990, 112, 323-333.
19. (c) Robl, J.; Cimarusti, M.; Simpkins, L.; Weller, H.; Pan, Y.; Malley, M.; DiMarco, J. J. Am. Chem. Soc. 1994, 116, 2348-2355.
20. 6. Boger, D. L.; Myers, Jr., J. B. J. Org. Chem. 1991, 56, 5385-5390.
21. 7. (a) Stella, L.; Abraham, H.; Feneau-Dupont, J.; Tinant, B.; Declercq, J. P. Tetrahedron Lett. 1990, 31, 2603-2606.
22. (b) Abraham, H.; Stella, L. Tetrahedron, 1992, 48, 9707-9718 .
23. (c) Abraham, H.; Théus, E.; Stella, L. Bull. Soc. Chim. Belg. 1994, 103, 361-366.
24. 8. Staudinger, H. Liebigs Ann. Chem. 1907, 356, 51-123.
25. 9. Reviews: (a) Cooper, R. D. G.; Daugherty, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485-492.
26. (b) Van der Steen, F. H.; Van Koten G. Tetrahedron 1991, 47, 7503-7524.
27. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I. Ed.; VCH: New York, 1993; pp 295-368.
28. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem., 1996, 61, 9186-9195.
29. 10. Williams, R. M., Ed., Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989.
30. 11. Bhattarai, K.; Cainelli, G.; Panunzio, M. Synlett, 1990, 229-230.
31. 12. a) Kronenthal, D. R., Han, C. Y., Taylor, M. K. J. Org. Chem. 1982, 47, 2765-2768.
32. b) Firestone, R. A.; Baarker, P. L.; Pisano, J. M.; Ashe, B. M.; Dahlgren, M. E. Tetrahedron, 1990, 46, 2255-2262.
33. 2O. These last experimental conditions were previously used by us : Bourzat, J. D.; Commerçon, A. Patent W. O. 94/24103 (27-10-1994).
34. 13. Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239-5242.
35. 14. Aszodi, J., Bonnet, A., Teutsch, G. Tetrahedron 1990, 46, 1579-1586.
36. 15. Ojima, I.; Suga, S.; Abe, R. Chem. Lett. 1980, 853-856.
37. 16. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3783-3786 & 3787-3790.
38. 17. a) De Marinis, R. M.; Bryan, W. M. Tetrahedron Lett. 1982, 23, 731-734.
39. b) Kishimoto, S.; Sendai, M.; Tomimoto, M.; Hashiguchi, S.; Matsuo, T.; Ochiai, M. Chem. Pharm. Bull. 1984, 32, 2646-2659.
40. c) Shiozaki, M.; Ishida, N.; Hiraoka, T.; Maruyama, H. Tetrahedron, 1984, 40, 1795-1802.
41. d) Sendai, M.; Hashiguchi, S.; Tomimoto, M.; Kishimoto, S.; Matsuo, T. Chem. Pharm. Bull. 1985, 33, 3798-3810.
42. e) Simig, G.; Fetter, J.; Hornyac, G.; Zauer, K.; Doleschall, G. Acta Chim. Hung. 1985, 119, 17-32.
43. f) Fetter, J.; Bertha, F.; Czuppon, T.; Kajtar-Peredy, M.; Lempert, K. J. Chem. Res. Miniprint, 1995, 11, 2738-2789.
44. g) Brown, S.; Jordan, A. M.; Lawrence, N. J.; Pritchard, R. G.; Mc Gown, A. T. Tet. Letters, 1998, 39, 3559-3562.
45. 18. We thank Dr. Y Christidis, Hoechst-France, Stains, for generous gift of methyl glyoxylate.
46. 19. Palomo, C., Aizpurua, J. M., Ontoria, J. M., Iturbruru, M. Tetrahedron Lett. 1992, 33, 4823-4826.
47. 20. Tubul, A.; Meou, A.; Bertrand, M. Tetrahedron Lett. 1983, 24, 4199-4202.
48. 21. Subasinghe, N., Schulte, M., Chan, M. Y. -M., Roon, R. J., Koerner, J. F., Johnson, R. L. J. Med. Chem. 1990, 33, 2734-2744.
49. 22. Palomo, C., Ontoria, J. M., Odriozola, J. M., Aizpurua, J. M., Ganboa, I. J. Chem. Soc., Chem. Commun. 1990, 248-249.
50. 23. Georg, G.I.; Wu, Z. Unpublished results, 1992, cited in Georg, G. I. The Organic Chemistry of β-lactams, Ed. Georg, G. I., VCH Pub., Inc., New York. 1993, p 224, ref 179.
51. 23. Georg, G.I.; Wu, Z. Unpublished results, 1992, cited in Georg, G. I. The Organic Chemistry of β-lactams, Ed. Georg, G. I., VCH Pub., Inc., New York. 1993, p 224, ref 179.
52. 24. a) Georg, G. I. The Organic Chemistry of β-lactams, Ed. Georg, G. I., VCH Pub., Inc., New York. 1993, pp 332-335.
53. b) Palomo, C.; Cossio, F. P. Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martinez-Ripoll M. J. Am. Chem. Soc. 1992, 114, 9360-9369.
54. c) Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995-1004.
55. 25. a) Gallo, R. in Progress in Physical Organic Chemistry, Taft, R.W., Ed.; Vol. 14, Wiley: New York, 1983, pp 115-163.
56. b) Gallo, R.; Roussel, C.; Berg, U. in Advances in Heterocyclic Chemistry, Katritsky, A.R., Ed.; Vol. 43, Academic Press: San Diego, 1988, pp. 173-299.
57. 26. a) Nishio, M.; Hirota, M. Tetrahedron, 1989, 45, 7201-7245.
58. b) Nishio, M.; Umezawa, M.; Hirota, M.; Takeuchi, Y. Tetrahedron, 1995, 51, 8665-8701.
59. 27. a) Sivanandaiah, K. M., Gurusiddappa, S. J. Chem. Res. (S), 1979, 108.
60. b) Bailey, P. D., Brown, G. R., Korber, F., Reed, A., Wilson, R. D. Tetrahedron Asymmetry 1991, 2, 1263.
61. c) Dugat, D., Just, G., Sahoo, S. Can. J. Chem. 1987, 65, 88-93.
62. d) Bourzat, J. D., Commerçon, A. Tetrahedron Lett. 1993, 34, 6049-6052.
63. 28. a) Teutsch, G., Bonnet, A. Tetrahedron Lett. 1984, 25, 1561-1562.
64. b) Annis, G. D., Hebblethwaite, E. M., Hodgson, S. T., Hollinshead, D. M., Ley, S. V; J. Chem. Soc., Perkin Trans. 1 1983, 2851-2856.
65. 29. Palomo, C., Aizpurua, J. M., Iturburu, R. G., Legido, M. Bioorg. Med. Chem. Lett. 1993, 3, 2461-2466.
66. 30. Manhas, M. S., Ghosh, M., Bose, A. K. J. Org. Chem. 1990, 55, 575-580.
67. 31. See, for exemple: Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381-384.
68. 32. a) Palomo, C.; Aizpurua, J. M.; Garcia, J.M.; Galarza, R.; Legido, M.; Urchegui, R.; Roman, P.; Luque, A.; Server-Carrio, J.; Linden, A. J. Org. Chem. 1997, 62, 2070-2079.
69. b) Palomo, C.; Aizpurua, J.M.; Legido, M.; Mielgo, A.; Galarza, R. Chem. Eur. J. 1997, 3, 1432-1441.
70. 33. Hubschwerlen, C., Specklin, J. L. In Organic Syntheses 1993, 72, 14-20.