Easy access to orthogonally protected α-alkyl aspartic acid and α-alkyl asparagine derivatives by controlled opening of β-lactams

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6145-6148

  Gerona Navarro, Guillermo ^a   García López, Ma Teresa ^a   González Muñiz, Rosario ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; ASPARAGINE DERIVATIVE; ASPARTIC ACID DERIVATIVE; BETA LACTAM DERIVATIVE; DIPEPTIDE; SODIUM AZIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0038305124     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01453-9     Document Type: Article

References (39)

1. α,α-disubstituted α-amino acids, see: (a) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (b) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
2. α,α-disubstituted α-amino acids, see: (a) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599; (b) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
3. Mcharfi M., Aubry A., Boussard G., Marraud M. Eur. Biophys J. 14:1986;43-51.
4. Warmus J.S., Ryder T.R., Hodges J.C., Kennedy R.M., Brady K.D. Bioorg. Med. Chem. Lett. 8:1998;2309-2314.
5. Mujica M.-T., Jung G. Synlett. 1999;1933-1935.
6. Seebach D., Studer A. Liebigs Ann. 1995;217-222.
7. Fadel A., Salaün J. Tetrahedron Lett. 28:1987;2243-2246.
8. Obrecht D., Bohdal U., Daly J., Lehmann C., Schönholzer P., Müller K. Tetrahedron. 51:1995;10883-10900.
9. Chinchilla R., Galindo N., Nájera C. Synthesis. 1999;704-717.
10. Ding K., Ma D. Tetrahedron. 57:2001;6361-6366.
11. Nájera C., Abellán T., Sansano J.M. Eur. J. Org. Chem. 2000;2809-2820.
12. Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228-5229.
13. Juaristi E., López-Ruiz H., Madrigal D., Ramírez-Quirós Y., Escalante J. J. Org. Chem. 63:1998;4706-4710.
14. Trost B.M., Ariza X. J. Am. Chem. Soc. 121:1999;10727-10737.
15. Sasaki H., Carreira E.M. Synthesis. 2000;135-138.
16. Palomo C., Aizpurua J.M., Ganboa I., Oiarbide M. Synlett. 2001;1813-1826.
17. Alcaide B., Almendros P. Synlett. 2002;381-393.
18. For methods on the preparation of β-amino acids from β-lactamas, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. In Enantoselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; pp. 279-357; (b) Ojima, I.; Delaloge, F. In Peptidomimetics Protocols; Kazmierski, W. M., Ed.; Humana Press: Totowa, 1998; pp. 137-170.
19. For methods on the preparation of β-amino acids from β-lactamas, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. In Enantoselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; pp. 279-357; (b) Ojima, I.; Delaloge, F. In Peptidomimetics Protocols; Kazmierski, W. M., Ed.; Humana Press: Totowa, 1998; pp. 137-170.
20. For the synthesis of β-amino ketones from β-lactamas, see: (a) Palomo, C.; Aizpurua, J. M.; García, J. M.; Iturburu, M.; Odriozola, J. M. J. Org. Chem. 1994, 59, 5184-5188; (b) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Smith, M. L.; Russel, A. T. Synlett 1993, 51-53; (c) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Vaughan, J. G. J. Chem. Soc., Chem. Commun. 1993, 1434-1435.
21. For the synthesis of β-amino ketones from β-lactamas, see: (a) Palomo, C.; Aizpurua, J. M.; García, J. M.; Iturburu, M.; Odriozola, J. M. J. Org. Chem. 1994, 59, 5184-5188; (b) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Smith, M. L.; Russel, A. T. Synlett 1993, 51-53; (c) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Vaughan, J. G. J. Chem. Soc., Chem. Commun. 1993, 1434-1435.
22. For the synthesis of β-amino ketones from β-lactamas, see: (a) Palomo, C.; Aizpurua, J. M.; García, J. M.; Iturburu, M.; Odriozola, J. M. J. Org. Chem. 1994, 59, 5184-5188; (b) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Smith, M. L.; Russel, A. T. Synlett 1993, 51-53; (c) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Vaughan, J. G. J. Chem. Soc., Chem. Commun. 1993, 1434-1435.
23. Alcaide B., Martín-Cantalejo Y., Pérez-Castells J., Sierra M.A., Monge A. J. Org. Chem. 61:1996;8819-8825.
24. Alcaide B., Almendros P., Alonso J.M., Aly M.F., Torres M.R. Synlett. 2001;1531-1534.
25. Alcaide B., Almendros P., Alonso J.M., Aly M.F. J. Org. Chem. 66:2001;1351-1358.
26. Romo D., Rzasa R.M., Shea H.A., Park K., Langenhan J.M., Sun L., Akhiezer A., Liu J.O. J. Am. Chem. Soc. 120:1998;12237-12254.
27. Cundy D.J., Donohue A.C., McCarthy T.D. Tetrahedron Lett. 39:1998;5125-5128.
28. Gardner B., Nakanishi H., Kahn M. Tetrahedron. 49:1993;3433-3448.
29. Gerona-Navarro G., Bonache M.A., Herranz R., García-López M.T., González-Muñiz R. Synlett. 2000;1249-1252.
30. Gerona-Navarro G., Bonache M.A., Herranz R., García-López M.T., González-Muñiz R. J. Org. Chem. 66:2001;3538-3547.
31. Gerona-Navarro G., Bonache M.A., Reyero N., García-López M.T., González-Muñiz R. Heterocycles. 57:2002;501-513.
32. tBu).
33. Sondheimer E., Holley R.W. J. Am. Chem. Soc. 76:1954;2467-2470.
34. Battersby A., Robinson J.C. J. Chem. Soc. 1955;259-269.
35. Tesser G.I., Buis J.T., Wolters E.T., Bothé-Helmes E.G. Tetrahedron. 32:1976;1069-1072.
36. Palomo C., Aizpurua J.M., Cuevas C. J. Chem. Soc., Chem. Commun. 1994;1957-1958.
37. Ojima I., Sun C.M., Park Y.H. J. Org. Chem. 59:1994;1249-1250.
38. Palomo C., Aizpurua J.M., Cuevas C., Mielgo A., Galarza R. Tetrahedron Lett. 36:1995;9027-9030.
39. Gerona-Navarro G., García-López M.T., González-Muñiz R. J. Org. Chem. 67:2002;3953-3956.