Unusual reaction of azetidine-2,3-diones with primary amines. Straightforward asymmetric synthesis of α-amino acid and peptide derivatives

Chemical Communications

Volumn , Issue 9, 2000, Pages 757-758

  Alcaide, Benito ^a   Almendros, Pedro ^a   Aragoncillo, Cristina ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINE; AZETIDINE DERIVATIVE; PEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034616522     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909688d     Document Type: Article

References (31)

1. For reviews, see: R. O. Duthaler, Tetrahedron, 1994, 50, 1539; R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; G. M. Coppola and H. F. Schuster, Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids, Wiley, New York, 1987.
2. For reviews, see: R. O. Duthaler, Tetrahedron, 1994, 50, 1539; R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; G. M. Coppola and H. F. Schuster, Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids, Wiley, New York, 1987.
3. For reviews, see: R. O. Duthaler, Tetrahedron, 1994, 50, 1539; R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989; G. M. Coppola and H. F. Schuster, Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids, Wiley, New York, 1987.
4. For selected examples, see: M. D. Struthers, R. P. Cheng and S. Imperiali, Science, 1995, 271, 342; J. W. Bryson, S. F. Betz, H. S. Lu, D. J. Suich, H. W. Zhou, R. T. O'Neil and W. F. Degrado, Science, 1995, 270, 935; M. W. Nowak, P. C. Kearney, J. R. Sampson, D. A. Dougherty and H. A. Lester, Science, 1995, 268, 439.
5. For selected examples, see: M. D. Struthers, R. P. Cheng and S. Imperiali, Science, 1995, 271, 342; J. W. Bryson, S. F. Betz, H. S. Lu, D. J. Suich, H. W. Zhou, R. T. O'Neil and W. F. Degrado, Science, 1995, 270, 935; M. W. Nowak, P. C. Kearney, J. R. Sampson, D. A. Dougherty and H. A. Lester, Science, 1995, 268, 439.
6. For selected examples, see: M. D. Struthers, R. P. Cheng and S. Imperiali, Science, 1995, 271, 342; J. W. Bryson, S. F. Betz, H. S. Lu, D. J. Suich, H. W. Zhou, R. T. O'Neil and W. F. Degrado, Science, 1995, 270, 935; M. W. Nowak, P. C. Kearney, J. R. Sampson, D. A. Dougherty and H. A. Lester, Science, 1995, 268, 439.
7. For reviews, see: A. Nangia and P. S. Chandrakala, Current Science, 1995, 68, 699; R. B. Silverman, Mechanism Based Enzyme Inactivation: Chemistry and Enzymology, CRC Press, Boca Raton, FL, 1988.
8. For reviews, see: A. Nangia and P. S. Chandrakala, Current Science, 1995, 68, 699; R. B. Silverman, Mechanism Based Enzyme Inactivation: Chemistry and Enzymology, CRC Press, Boca Raton, FL, 1988.
9. For representative examples, see: Y. S. Cho, J. E. Lee and H. Y. Koh, Tetrahedron Lett., 1999, 40, 1725; J. D. Buynak, H. B. Borate, G. W. Lamb, D. D. Khasnis, C. Husting, H. Isom and U. Sriwardane, J. Org. Chem., 1993, 58, 1325; D. G. Brenner, J. Org. Chem., 1985, 50, 18.
10. For representative examples, see: Y. S. Cho, J. E. Lee and H. Y. Koh, Tetrahedron Lett., 1999, 40, 1725; J. D. Buynak, H. B. Borate, G. W. Lamb, D. D. Khasnis, C. Husting, H. Isom and U. Sriwardane, J. Org. Chem., 1993, 58, 1325; D. G. Brenner, J. Org. Chem., 1985, 50, 18.
11. For representative examples, see: Y. S. Cho, J. E. Lee and H. Y. Koh, Tetrahedron Lett., 1999, 40, 1725; J. D. Buynak, H. B. Borate, G. W. Lamb, D. D. Khasnis, C. Husting, H. Isom and U. Sriwardane, J. Org. Chem., 1993, 58, 1325; D. G. Brenner, J. Org. Chem., 1985, 50, 18.
12. L. A. Paquette and M. B. Isaac, Heterocycles, 1998, 47, 107; M. Jayaraman, M. S. Manhas and A. K. Bose, Tetrahedron Lett., 1997, 38, 709.
13. L. A. Paquette and M. B. Isaac, Heterocycles, 1998, 47, 107; M. Jayaraman, M. S. Manhas and A. K. Bose, Tetrahedron Lett., 1997, 38, 709.
14. L. A. Paquette, R. R. Rothhaar, M. Isaac, L. M. Rogers and R. D. Rogers, J. Org. Chem., 1998, 63, 5463; S. T. Hodgson, D. M. Hollinshead, S. V. Ley, C. M. R. Low and D. J. Willians, J. Chem. Soc., Perkin Trans., 1, 1985, 2375.
15. L. A. Paquette, R. R. Rothhaar, M. Isaac, L. M. Rogers and R. D. Rogers, J. Org. Chem., 1998, 63, 5463; S. T. Hodgson, D. M. Hollinshead, S. V. Ley, C. M. R. Low and D. J. Willians, J. Chem. Soc., Perkin Trans., 1, 1985, 2375.
16. For selected examples of the potential of β-lactams as intermediates for the access to α- and β-amino acid-derived peptides, see: C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Amino Acids, 1999, 16, 321; C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda and A. Linden, J. Org. Chem., 1998, 63, 5838; C. Palomo, I. Ganboa, B. Odriozola and A. Linden, Tetrahedron Lett., 1997, 38, 3093; C. Palomo, M. Oiarbide and A. Esnal, Chem. Commun., 1997,691; C. Palomo, J. M. Aizpurua, I. Ganboa, F. Carreaux, C. Cuevas, E. Maneiro and J. M. Ontoria, J. Org. Chem., 1994, 59, 3123; F. P. Cossio, C. López, M. Oiarbide, C. Palomo, D. Aparicio and G. Rubiales, Tetrahedron Lett., 1988, 29, 3133.
17. For selected examples of the potential of β-lactams as intermediates for the access to α- and β-amino acid-derived peptides, see: C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Amino Acids, 1999, 16, 321; C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda and A. Linden, J. Org. Chem., 1998, 63, 5838; C. Palomo, I. Ganboa, B. Odriozola and A. Linden, Tetrahedron Lett., 1997, 38, 3093; C. Palomo, M. Oiarbide and A. Esnal, Chem. Commun., 1997,691; C. Palomo, J. M. Aizpurua, I. Ganboa, F. Carreaux, C. Cuevas, E. Maneiro and J. M. Ontoria, J. Org. Chem., 1994, 59, 3123; F. P. Cossio, C. López, M. Oiarbide, C. Palomo, D. Aparicio and G. Rubiales, Tetrahedron Lett., 1988, 29, 3133.
18. For selected examples of the potential of β-lactams as intermediates for the access to α- and β-amino acid-derived peptides, see: C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Amino Acids, 1999, 16, 321; C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda and A. Linden, J. Org. Chem., 1998, 63, 5838; C. Palomo, I. Ganboa, B. Odriozola and A. Linden, Tetrahedron Lett., 1997, 38, 3093; C. Palomo, M. Oiarbide and A. Esnal, Chem. Commun., 1997,691; C. Palomo, J. M. Aizpurua, I. Ganboa, F. Carreaux, C. Cuevas, E. Maneiro and J. M. Ontoria, J. Org. Chem., 1994, 59, 3123; F. P. Cossio, C. López, M. Oiarbide, C. Palomo, D. Aparicio and G. Rubiales, Tetrahedron Lett., 1988, 29, 3133.
19. For selected examples of the potential of β-lactams as intermediates for the access to α- and β-amino acid-derived peptides, see: C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Amino Acids, 1999, 16, 321; C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda and A. Linden, J. Org. Chem., 1998, 63, 5838; C. Palomo, I. Ganboa, B. Odriozola and A. Linden, Tetrahedron Lett., 1997, 38, 3093; C. Palomo, M. Oiarbide and A. Esnal, Chem. Commun., 1997,691; C. Palomo, J. M. Aizpurua, I. Ganboa, F. Carreaux, C. Cuevas, E. Maneiro and J. M. Ontoria, J. Org. Chem., 1994, 59, 3123; F. P. Cossio, C. López, M. Oiarbide, C. Palomo, D. Aparicio and G. Rubiales, Tetrahedron Lett., 1988, 29, 3133.
20. For selected examples of the potential of β-lactams as intermediates for the access to α- and β-amino acid-derived peptides, see: C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Amino Acids, 1999, 16, 321; C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda and A. Linden, J. Org. Chem., 1998, 63, 5838; C. Palomo, I. Ganboa, B. Odriozola and A. Linden, Tetrahedron Lett., 1997, 38, 3093; C. Palomo, M. Oiarbide and A. Esnal, Chem. Commun., 1997,691; C. Palomo, J. M. Aizpurua, I. Ganboa, F. Carreaux, C. Cuevas, E. Maneiro and J. M. Ontoria, J. Org. Chem., 1994, 59, 3123; F. P. Cossio, C. López, M. Oiarbide, C. Palomo, D. Aparicio and G. Rubiales, Tetrahedron Lett., 1988, 29, 3133.
21. For selected examples of the potential of β-lactams as intermediates for the access to α- and β-amino acid-derived peptides, see: C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide, Amino Acids, 1999, 16, 321; C. Palomo, M. Oiarbide, A. Esnal, A. Landa, J. I. Miranda and A. Linden, J. Org. Chem., 1998, 63, 5838; C. Palomo, I. Ganboa, B. Odriozola and A. Linden, Tetrahedron Lett., 1997, 38, 3093; C. Palomo, M. Oiarbide and A. Esnal, Chem. Commun., 1997,691; C. Palomo, J. M. Aizpurua, I. Ganboa, F. Carreaux, C. Cuevas, E. Maneiro and J. M. Ontoria, J. Org. Chem., 1994, 59, 3123; F. P. Cossio, C. López, M. Oiarbide, C. Palomo, D. Aparicio and G. Rubiales, Tetrahedron Lett., 1988, 29, 3133.
22. B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Commun., 1999, 1913; B. Alcaide, I. M. Rodríguez-Campos, J. Rodríguez-López and A. Rodríguez-Vicente, J. Org. Chem., 1999, 64, 5377; B. Alcaide and P. Almendros, Tetrahedron Lett., 1999, 40, 1015; B. Alcaide, J. M. Alonso, M. A. Aly, E. Sáez, M. P. Martínez-Alcázar and F. Hernández-Cano, Tetrahedron Lett., 1999, 40, 5391.
23. B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Commun., 1999, 1913; B. Alcaide, I. M. Rodríguez-Campos, J. Rodríguez-López and A. Rodríguez-Vicente, J. Org. Chem., 1999, 64, 5377; B. Alcaide and P. Almendros, Tetrahedron Lett., 1999, 40, 1015; B. Alcaide, J. M. Alonso, M. A. Aly, E. Sáez, M. P. Martínez-Alcázar and F. Hernández-Cano, Tetrahedron Lett., 1999, 40, 5391.
24. B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Commun., 1999, 1913; B. Alcaide, I. M. Rodríguez-Campos, J. Rodríguez-López and A. Rodríguez-Vicente, J. Org. Chem., 1999, 64, 5377; B. Alcaide and P. Almendros, Tetrahedron Lett., 1999, 40, 1015; B. Alcaide, J. M. Alonso, M. A. Aly, E. Sáez, M. P. Martínez-Alcázar and F. Hernández-Cano, Tetrahedron Lett., 1999, 40, 5391.
25. B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Commun., 1999, 1913; B. Alcaide, I. M. Rodríguez-Campos, J. Rodríguez-López and A. Rodríguez-Vicente, J. Org. Chem., 1999, 64, 5377; B. Alcaide and P. Almendros, Tetrahedron Lett., 1999, 40, 1015; B. Alcaide, J. M. Alonso, M. A. Aly, E. Sáez, M. P. Martínez-Alcázar and F. Hernández-Cano, Tetrahedron Lett., 1999, 40, 5391.
26. B. Alcaide, P. Almendros and C. Aragoncillo, Tetrahedron Lett., 1999, 40, 7537.
27. Ojima et al. have developed a smart methodology for the synthesis of peptides and peptidomimetics starting from enantiopure 2-azetidinones by means of the β-lactam synthon method. See: I. Ojima and F. Delaloge, Chem. Soc. Rev., 1997, 26, 377; I. Ojima, Adv. Asymmetric Synth., 1995, 1, 95.
28. Ojima et al. have developed a smart methodology for the synthesis of peptides and peptidomimetics starting from enantiopure 2-azetidinones by means of the β-lactam synthon method. See: I. Ojima and F. Delaloge, Chem. Soc. Rev., 1997, 26, 377; I. Ojima, Adv. Asymmetric Synth., 1995, 1, 95.
29. B. Alcaide, G. Esteban, Y. Martín-Cantalejo, J. Plumet, J. Rodríguez-López, A. Monge and V. Pérez-García, J. Org. Chem., 1994, 59, 7994.
30. J. W. Skiles and D. McNeil, Tetrahedron, 1990, 31, 7277.
31. 3N (cat.) in methanol: J. M. Aizpurua, F. P. Cossío and C. Palomo, Tetrahedron Lett., 1986, 27, 4359. According to the proposed mechanism some evolution of CO is expected in the course of the process. However, we believe that the reaction is carried out on a small scale (0.5 mmol) and is too slow to observe any appreciable gas evolution.