Alternative and chemoselective deprotection of the α-amino and carboxy functions of N-Fmoc-amino acid and N-Fmoc-dipeptide methyl esters by modulation of the molar ratio in the AlCl3/N,N-dimethylaniline reagent system

European Journal of Organic Chemistry

Volumn , Issue 21, 2004, Pages 4437-4441

  Di Gioia, Maria Luisa ^a   Leggio, Antonella ^a   Le Pera, Adolfo ^a   Liguori, Angelo ^a   Perri, Francesca ^a   Siciliano, Carlo ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Aluminium trichloride; Amino acids; Deprotection; Dipeptides; N,N Dimethylaniline

Indexed keywords

ESTER DERIVATIVE; LEWIS ACID; N FLUORENYLMETHYLOXYCARBONYLPHENYLALANINE METHYLESTER; N FLUORENYLMETHYLOXYCARBONYLTYROSINE METHYLESTER; N,N DIMETHYLANILINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION;

EID: 8144229851     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400321     Document Type: Article

References (24)

1. For a comprehensive review, see: E. Haslam, Tetrahedron 1980, 36, 2409-2434.
2. R. W. Roeske, The Peptides, Academic Press, New York, 1981, vol. 3, p. 102.
3. J. Jones, The Chemical Synthesis of Peptides, Clarendon Press, Oxford, 1991, p. 103.
4. M. Bodanzski, Principles of Peptide Synthesis, Springer-Verlag, Berlin, 1984, 2nd ed., p. 221.
5. S. Liu, C. Dockendorff, S. D. Taylor, Org. Lett. 2001, 3, 1571-1574.
6. B. Ye, T. R. Burke, Tetrahedron Lett. 1995, 36, 4733-4736.
7. R. Pascal, R. Sola, Tetrahedron Lett. 1998, 39, 5031-5034.
8. M. G. Organ, J. Xu, B. N'Zemba, Tetrahedron Lett. 2002, 43, 8177-8180.
9. R. W. Jackson, Tetrahedron Lett. 2001, 42, 5163-5165.
10. M. J. O'Donnell, F. Delgado, Tetrahedron 2001, 57, 6641-6650.
11. Y-Q. Wu, D. C. Limburg, D. E. Wilkinson, M. J. Vaal, G. S. Hamilton, Tetrahedron Lett. 2000, 41, 2847-2849.
12. G. M. Makara, G. R. Marshall, Tetrahedron Lett. 1997, 38, 5069-5072.
13. C. W. West, M. A. Estiarte, D. H. Rich, Org. Lett. 2001, 3, 1205-1208.
14. D. Filippov, E. K. Yeheskiely, G. A. van der Marel, G. I. Tesser, J. H. van Boom, Tetrahedron Lett. 1998, 39, 3597-3600.
15. K. J. Hale, J. Cai, V. M. Delisser, Tetrahedron Lett. 1996, 37, 9345-9348.
16. W.-C. Chen, M. D. Vera, M. M. Joullie, Tetrahedron Lett. 1997, 38, 4025-4028.
17. M. Nishizawa, H. Yamamoto, K. Seo, H. Imagawa, T. Sugihara, Org. Lett. 2002, 4, 1947-1949.
18. Y. Luo, M. A. Blaskovich, G. A. Lajoie, J. Org. Chem. 1999, 64, 6106-6111.
19. P. Gomez-Martinez, A. M. Kimbonguila, F. Guibe, Tetrahedron 1999, 55, 6945-6960.
20. J. M. Sanderson, P. Singh, C. W. G. Fishwick, J. B. C. Findlay, J. Chem. Soc., Perkin Trans. 1 2000, 3227-3231.
21. J. M. Caba, I. M. Rodriguez, I. Manzanares, E. Giralt, F. Albericio, J. Org. Chem. 2001, 66, 7568-7574.
22. M. L. Di Gioia, A. Leggio, A. Le Pera, C. Siciliano, G. Sindona, A. Liguori, J. Pept. Res. 2004, 63, 383-387.
23. A. Leggio, A. Liguori, A. Napoli, C. Siciliano, G. Sindona, Eur. J. Org. Chem. 2000, 573-575.
24. M. L. Di Gioia, A. Leggio, A. Liguori, A. Napoli, C. Siciliano, G. Sindona, J. Org. Chem. 2001, 66, 7002-7007.