Diastereoselective strecker reaction of D-glyceraldehyde derivatives. A novel route to (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid

Tetrahedron

Volumn 52, Issue 28, 1996, Pages 9563-9574

  Cativiela, Carlos ^a   Díaz De Villegas, María D ^a   Gálvez, José A ^a   García, José I ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3,4 DIHYDROXYBUTYRIC ACID; GLYCERALDEHYDE; HYDROXYBUTYRIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030575429     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00493-0     Document Type: Article

References (49)

1. (1) For leading references on the stereoselective synthesis of β-hydroxy-α-amino acids see: (a) Hirama, M.; Hioki, H.; Ito, S., Tetrahedron Lett., 1988, 29, 3125.
2. (b) Cardani, S.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C.; Venturini, I., Tetrahedron, 1988, 44, 5563.
3. (c) Roemmele, R. C.; Rapoport, H., J. Org. Chem., 1989, 54, 1866.
4. (d) van der Werf, A. W.; Kellogg, R. M.; van Bolhuis, F., J. Chem. Soc., Chem. Commun., 1991, 682.
5. (e) Ohfune, Y., Acc. Chem. Res., 1992, 25, 360.
6. (f) Hanessian, S.; Vanasse, B., Can. J. Chem., 1993, 71, 1401.
7. (g) Blaskovich, M. A.; Lajoie, G. A., J. Am. Chem. Soc., 1993, 115, 5021.
8. (h) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R., J. Org. Chem., 1995, 60, 6431.
9. (i) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Tararov, V. I.; Savel'eva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon, Y. N., Tetrahedron: Asymmetry, 1995, 6, 1741.
10. (2) See for example: (a) "Amino Acids, Peptides and Proteins. The Chemical Society: Cambridge, 1968-1991; Vols 1-22.
11. (b) Wenger, R. M., Angew. Chem., Int. Ed. Engl., 1985, 24, 77.
12. (c) Passerat, N.; Bolte, J., Tetrahedron Lett., 1987, 28, 1277.
13. (d) Evans, D. A.; Weber, A. E., J. Am. Chem. Soc., 1987, 109, 7151.
14. (e) Tymiak, A. A.; McCormick, T. J.; Unger, S. E., J. Org. Chem., 1989, 54, 1149.
15. (3) See for example: (a) Holden, K. G. in "Cephalosporins and Penicillins: Chemistry and Biology", Flynn, E. H., Ed; Academic Press: New York, 1972 Vol 2.
16. (b) Floyd, D. M.; Fritz, A. W.; Pluscec, J.; Weaver, E. R.; Cimarusti, C. M., J. Org. Chem., 1982, 47, 5160.
17. (c) Labia, R.; Morin, C., J. Antibiotics, 1984, 37, 1103.
18. (d) Wei, C. C.; De Bernardo, S.; Tengi, J. P.; Borgese, J.; Weigele, M., J. Org. Chem., 1985, 50, 3462.
19. (e) Christenson, J.; Squires, E., Drugs of the Future, 1985, 10, 967.
20. (f) Banfi, L.; Cascio, G.; Guanti, G.; Manghishi, E.; Narisano, E.; Riva, R., Tetrahedron, 1994, 50, 11967.
21. (g) Banfi, L.; Cascio, G.; Ghiron, C.; Guanti, G.; Manghishi, E.; Narisano, E.; Riva, R., Tetrahedron, 1994, 50, 11983.
22. (4) (a) Matsuura, F.; Hamada, Y.; Shioiri, T., Tetrahedron, 1994, 50, 265.
23. (b) Shioiri, T.; Hamada, Y.; Matsuura, F., Tetrahedron, 1995, 51, 3939.
24. (5) Jurczak, J.; Pikul, S.; Bauer, T., Tetrahedron, 1986, 42, 447.
25. (6) For a recent review and recent papers on stereoselective Strecker type reactions see: (a) Duthaler, R. O., Tetrahedron, 1994, 50, 1539.
26. (b) Kunz, H., Pure and Applied Chemistry, 1995, 67, 1627.
27. (c) Chakraborty, T. K.; Azhar Hussain, K.; Venkat Reddy, G., Tetrahedron, 1995, 51, 9179.
28. (d) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. H., J. Org. Chem., 1996, 61, 440.
29. (7) Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A., Tetrahedron Lett., 1995, 36, 2859.
30. (8) (a) Zandbergen, P.; Brussee, J.; van der Gen, A.; Kruse, C. G., Tetrahedron: Asymmetry, 1992, 3, 769.
31. (b) Cainelli, G.; Giacomini, D.; Treré, A.; Galleti, P., Tetrahedron: Asymmetry, 1995, 6, 1593.
32. (9) Kunz, H.; Sager, W.; Pfrengle, W.; Schanzenbach, D., Tetrahedron Lett., 1988, 29, 4397.
33. (10) (a) Reetz, M. T.; Kesseler, K.; Jung, A., Angew. Chem., Int. Ed. Engl., 1985, 24, 989.
34. (b) Reetz, M. T.; Drewes, M. W.; Hars, K.; Reif, W., Tetrahedron Lett., 1988, 29, 3295.
35. (11) Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C. H., Tetrahedron Lett., 1995, 36, 5063.
36. (12) Cram, D. J.; Abd Elhafez, F. A., J. Am. Chem. Soc., 1952, 74 5828.
37. (13) (a) Cherest, M.; Felkin, H.; Prudent, N., Tetrahedron Lett., 1968, 2199.
38. (b) Cherest, M.; Felkin, H., Tetrahedron Lett., 1968, 2205.
39. (14) (a) Anh, N. T.; Eisenstein, O., Nouv. J. Chim., 1977, 1, 61.
40. (b) Anh, N. T., Fortschr. Chem. Forschung., 1980, 88, 145.
41. (15) (a) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N., J. Am. Chem. Soc., 1982, 104, 7162.
42. (b) Wu, Y.-D.; Houk, K. N., J. Am. Chem. Soc., 1987, 109, 908.
43. (c) Wong, S. S.; Paddon-Row, M. N., J. Chem. Soc., Chem. Commun., 1991, 327.
44. (16) Anh, N. T.; Maurel, F.; Lefour, J.-M., New J. Chem., 1995, 19, 353.
45. (17) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P., J. Am. Chem. Soc., 1985, 107, 3902.
46. (18) Ashton, W. T.; Canning, L. F.; Reynolds, G. F.; Tolman, R. L.; Karkas, J. D.; Liou, R.; Davies, M.-E. M.; Dewilt, C. M., Preey, H. C.; Field, A. K., J. Med. Chem., 1985, 28, 926.
47. (19) Stewart, J. J. P., MOPAC 6.0 (QCPE 455)
48. (20) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Repogle, E. S.; Gomperts, R.; Andrés, J. L.; Raghavachari, K.; Binkley, J. S.; González, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A., GAUSSIAN 92, Revision D.2, Gaussian Inc., Pittsburgh, PA 1992.
49. (21) Schelegel, H. B., J. Comput. Chem., 1982, 3, 214.