Efficient stereodivergent synthesis of cis-(2R,4S)- and trans-(2R,4R)-4-phosphonomethyl-2-piperidinecarboxylic acids from the same chiral imine derived from (R)-glyceraldehyde

Synlett

Volumn , Issue 17, 2006, Pages 2799-2803

  Etayo, Pablo ^a   Badorrey, Ramón ^a   Díaz De Villegas, María D ^a   Gálvez, José A ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Amino acids; Asymmetric synthesis; Phosphonates; Piperidines; Stereoselective reductions

Indexed keywords

4 PHOSPHONOMETHYLPIPECOLIC ACID; EXOCYCLIC DOUBLE BOND; GLYCERALDEHYDE; IMINE; N [ 1 PHENYLETHYL] 2,3 DI O BENZYLGLYCERALDIMINE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; STEREOCHEMISTRY;

EID: 33750501367     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950272     Document Type: Article

References (28)

1. (a) Lehmann, J.; Hutchison, A. J.; McPherson, S. E.; Mondadori, C.; Schmutz, M.; Sinton, C. M.; Tsai, C.; Murphy, D. E.; Steel, D. J.; Williams, M.; Cheney, D. L.; Wood, P. L. J. Pharmacol. Exp. Ther. 1988, 246, 65.
2. (b) Ornstein, P. L.; Schaus, J. M.; Chambers, J. W.; Huser, D. L.; Leander, J. D.; Wong, D. T.; Paschal, J. W.; Jones, N. D.; Deeter, J. B. J. Med. Chem. 1989, 32, 827.
3. (c) Miur, K. W.; Lees, F. R. Stroke 1995, 26, 503.
4. Hutchison, A. J.; Williams, M.; Angst, C.; de Jesus, R.; Blanchard, L.; Jackson, R. H.; Wilusz, E. J.; Murphy, D. E.; Bernard, P. S.; Schneider, J.; Campbell, T.; Guida, W.; Sills, M. A. J. Med. Chem. 1989, 32, 2171.
5. Baudy, R. B.; Fletcher, H. III; Yardley, J. P.; Zaleska, M. M.; Bramlett, D. R.; Tasse, R. P.; Kowal, D. M.; Katz, A. H.; Moyer, J. A.; Abou-Gharbia, M. J. Med. Chem. 2001, 44, 1516; and references cited therein.
6. (a) Davis, S. M.; Lees, K. R.; Albers, G. W.; Diener, H. C.; Markabi, S.; Karlsson, G.; Norris, J. Stroke 2000, 31, 347.
7. (b) Ikonomidou, C.; Turski, C. Lancet Neurol. 2002, 1, 383.
8. (c) Hoyte, L.; Barber, P. A.; Buchan, A. M.; Hill, M. D. Curr. Mol. Med. 2004, 4, 131.
9. Skiles, J. W.; Giannousis, P. P.; Fales, K. R. Bioorg. Med. Chem. Lett. 1996, 6, 963.
10. Badorrey, R.; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron 1999, 55, 7601.
11. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfield, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
12. In the absence of LiCl the HWE olefination reaction using DBU as base did not take place.
13. 5P: 578.3030; found: 578.3034.
14. 31P analyses of the crude reaction mixture.
15. 5P: 580.3186; found: 580.3192.
16. 7PNa: 418.1965; found: 418.1973.
17. 2 for 48 h. After completion of the reaction, the mixture was filtered through Celite® 545 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography.
18. 4 and the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica gel (eluent: EtOAc-EtOH, 4:1).
19. 7PNa: 402.1652; found: 402.1647.
20. 2O, 1:1) and lyophilized.
21. 5P: C, 37.67; H, 6.32; N, 6.28. Found: C, 37.58; H, 6.37; N, 6.23.
22. Martin, I.; Anvelt, J.; Vares, L.; Kühn, I.; Claesson, A. Acta Chem. Scand. 1995, 49, 230.
23. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry: Structure and Mechanisms, Part A, 4th ed.; Springer Science: New York, 2000.
24. Badorrey, R.; Cativiela, C.; Díaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron 2002, 58, 341.
25. 5P: 580.3186; found: 580.3174.
26. 7PNa: 418.1965; found: 418.1976.
27. 7PNa: 402.1652; found: 402.1651.
28. 5P: C, 37.67; H, 6.32; N, 6.28. Found: C, 37.56; H, 6.24; N, 6.33.