Stereocontrolled synthesis of 3-substituted azetidinic amino acids

Synlett

Volumn , Issue 5, 2006, Pages 781-785

  Sivaprakasam, Mangaleswaran ^a   Couty, François ^a   Evano, Gwilherm ^a   Srinivas, B ^b   Sridhar, R ^b   Rao, K Rama ^b  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Amino acids; Amino alcohols; Asymmetric synthesis; Azetidines

Indexed keywords

AMINO ACID DERIVATIVE; AZETIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; SYNTHESIS;

EID: 33645410513     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-933125     Document Type: Article

References (25)

1. Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297.
2. (a) Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2003, 44, 5209.
3. (b) Couty, F.; Durrat, F.; Evano, G.; Prim, D. Tetrahedron Lett. 2004, 45, 7525.
4. Couty, F.; Durrat, F.; Evano, G. Synlett 2005, 1666.
5. Couty, F.; Evano, G.; Rabasso, N. Tetrahedron: Asymmetry 2003, 14, 2407.
6. Agami, C.; Couty, F.; Rabasso, N. Tetrahedron Lett. 2002, 43, 4633.
7. Bräuner-Osborne, H.; Bunch, L.; Chopin, N.; Couty, F.; Evano, G.; Jensen, A. A.; Kusk, M.; Nielsen, B.; Rabasso, N. Org. Biomol. Chem. 2005, 3, 3926.
8. For related examples of chlorination of β-amino alcohols, see: (a) Weber, K.; Kuklinski, S.; Gmeiner, P. Org. Lett. 2000, 2, 647.
9. (b) Chong, H.; Ganguly, B.; Broker, G. A.; Rogers, R. D.; Brechbiel, M. W. J. Chem. Soc., Perkin Trans. 1 2002, 2080.
10. (c) Couty, F.; Evano, G.; Prim, D. Tetrahedron Lett. 2005, 46, 2253.
11. For other syntheses of azetidinic α-amino acids, see: (a) Kozikowski, A. P.; Tückmantel, W.; Reynolds, I. J.; Wrobleski, J. T. J. Med. Chem. 1990, 33, 1561.
12. (b) Kozikowski, A. P.; Liao, Y.; Tückmantel, W.; Wang, S.; Pshenichkin, S.; Surin, A.; Thomsen, C.; Wrobleski, J. T. J. Bioorg. Med. Chem. Lett. 1996, 6, 2559.
13. (c) Hanessian, S.; Fu, J. M.; Chiara, J.-L.; Di Fabio, R. Tetrahedron Lett. 1993, 34, 4157.
14. (d) Hanessian, S.; Bernstein, N.; Yang, R.-Y.; Maguire, R. Bioorg. Med. Chem. Lett. 1999, 9, 1437.
15. (e) Couty, F.; Evano, G.; Rabasso, N. Tetrahedron: Asymmetry 2003, 14, 2407.
16. (f) Jiang, J.; Shah, H.; DeVita, R. J. Org. Lett. 2003, 5, 4101.
17. (g) Gerona-Navarro, G.; Angeles Bonache, M.; Alías, M.; Pérez de Vega, M. J.; García-López, T.; Pilar López, M.; Cativiela, C.; González-Muñiz, R. Tetrahedron Lett. 2004, 45, 2193.
18. (h) Sajjadi, Z.; Lubell, W. D. J. Peptide Res. 2005, 65, 298.
19. (i) Couty, F.; Evano, G.; Vargas-Sanchez, M.; Bouzas, G. J. Org. Chem. 2005, 70, 9028.
20. Hart, P. A.; Rich, D. H. In The Practice of Medicinal Chemistry, 3rd ed.; Wermuth, C. G., Ed.; Academic Press: London, 2000.
21. Čaplar, V.; Raza, Z.; Katalenić, D.; Žinić, M. Croat. Chem. Acta 2003, 76, 23.
22. Rajender Reddy, L.; Bhanumati, N.; Rama Rao, K. Chem. Commun. 2000, 2321.
23. Concellón, J. M.; Pablo, L. B.; Pérez-Andrés, J. A. Tetrahedron Lett. 2000, 41, 1231.
24. Pirkle, W. H.; Hoekstra, M. S. J. Am. Chem. Soc. 1976, 98, 1832.
25. 2 (%): C, 73.53; H, 8.87; N, 5.36. Found: C, 73.39; H, 9.01; N, 5.42.