Synthesis of chiral α-amino-diazoketones on solid support: An access to β-homologated amino acid derivatives

Synlett

Volumn , Issue 15, 2004, Pages 2791-2793

  Cantel, Sonia ^a   Martinez, Jean ^a   Fehrentz, Jean Alain ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

amino diazoketone; Inverse anchoring; Solid phase synthesis; Wolff rearrangement

Indexed keywords

AMIDE; AMINE; BETA AMINO ACID; DIAZOMETHANE; DIAZONIUM COMPOUND; KETONE DERIVATIVE; RESIN; WATER;

AMINO TERMINAL SEQUENCE; ARTICLE; CHIRALITY; REACTION ANALYSIS; SOLID; SYNTHESIS; WOLFF REARRANGEMENT;

EID: 10844264058     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-835639     Document Type: Article

References (10)

1. Penke, B.; Czombos, J.; Balaspiri, L.; Peters, J.; Kovacs, K. Helv. Chim. Acta 1970, 53, 1057.
2. Groarke, M.; McKervey, M. A.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1275.
3. Groarke, M.; McKervey, M. A.; Moncrieff, H.; Nieuwenhuyzen, M. Tetrahedron Lett. 2000, 41, 1279.
4. Umezawa, H.; Nakamura, T.; Fukatsu, S.; Aoyagi, T.; Tatsuta, K. J. Antibiot. 1983, 36, 1787.
5. Gouilleux, L.; Fehrentz, J.-A.; Winternitz, F.; Martinez, J. Tetrahedron Lett. 1996, 37, 7031.
6. Cantel, S.; Desgranges, S.; Martinez, J.; Fehrentz, J.-A. J. Pept. Sci. 2004, 10, 326.
7. For a revue of activating reagents see: Synthesis of Peptides and Peptidomimetics, In Houben-Weyl, Methods of Organic Chemistry, Vol. E22c; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Thieme: Stuttgart, 2002.
8. Babu, V. V. S.; Gopi, H. N. J. Pept. Res. 1999, 53, 308.
9. Babu, V. V. S.; Gopi, H. N. Lett. Pept. Sci. 1999, 6, 173.
10. Plucinska, K.; Liberek, B. Tetrahedron Lett. 1987, 15, 3509.