Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

Tetrahedron

Volumn 62, Issue 35, 2006, Pages 8404-8409

  Reyes Rangel, Gloria ^a   Marañón, Virginia ^a   Avila Ortiz, C Gabriela ^a   Anaya de Parrodi, Cecilia ^b   Quintero, Leticia ^c   Juaristi, Eusebio ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b UNIVERSIDAD DE LAS AMÉRICAS PUEBLA   (Mexico)

^c BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

Author keywords

Aminophosphonic acids; Chiral oxazolidinones; Diastereoselective electrophilic amination; Enantioselective synthesis

Indexed keywords

2 AMINO 3 PHOSPHONOPROPIONIC ACID; 2 AMINO 4 PHOSPHONOPROPIONIC ACID; CARBOXYLIC ACID DERIVATIVE; N [3' (DIETHOXYPHOSPHORYL)PROPIONYL]HEXAHYDROBENZOXAZOLIDIN 2 ONE; N [4' (DIETHOXYPHOSPHORYL)BUTANOYL]HEXAHYDROBENZOXAZOLIDIN 2 ONE; OXAZOLIDINONE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; HYDROLYSIS; PRIORITY JOURNAL;

EID: 33745950121     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.06.018     Document Type: Article

References (43)

1. Ferkany J.W., Willetts J., Borosky S.A., Clissold D.B., Karbon E.W., and Hamilton G.S. Bioorg. Med. Chem. Lett. 3 (1993) 33
2. Young A.B., Greenamyre J.T., Hollingsworth Z., Albin R., D'Amato C., Shoulson I., and Penny J.B. Science 241 (1988) 981
3. Collingridge G.L., and Singer W. Trends Pharmacol. Sci. 11 (1990) 290
4. Klockgether T., and Turski L. Ann. Neurol. 28 (1990) 539
5. Zivin J.A., and Choi D.W. Sci. Am. 265 (1991) 56
6. Rosowsky A., Forsch R.A., Moran R.G., Kohler W., and Freisheim J.H. J. Med. Chem. 31 (1988) 1326
7. Schoepp D.D., and Johnson B.G. J. Neurochem. 53 (1989) 1865
8. Koerner J.F., and Cotman C.W. Brain Res. 216 (1981) 192
9. See, for example:
10. Ornstein P.L. J. Org. Chem. 54 (1989) 2251
11. Muller M., Mann A., and Taddei M. Tetrahedron Lett. 34 (1993) 3289
12. García-Barradas O., and Juaristi E. Tetrahedron 51 (1995) 3423
13. García-Barradas O., and Juaristi E. Tetrahedron: Asymmetry 8 (1997) 1511
14. Anaya de Parrodi C., Juaristi E., Quintero L., and Clara-Sosa A. Tetrahedron: Asymmetry 8 (1997) 1075
15. For a review, see:. Anaya de Parrodi C., and Juaristi E. Synlett (2006) in press
16. For recent reviews on the use of (R)- and (S)-α-phenylethylamine in the preparation of enantiopure compounds, see:
17. Juaristi E., Escalante J., León-Romo J.L., and Reyes A. Tetrahedron: Asymmetry 9 (1998) 715
18. Juaristi E., León-Romo J.L., Reyes A., and Escalante J. Tetrahedron: Asymmetry 10 (1999) 2441
19. Anaya de Parrodi C., Clara-Sosa A., Pérez L., Quintero L., Marañón V., Toscano R.A., Aviña J.A., Rojas-Lima S., and Juaristi E. Tetrahedron: Asymmetry 12 (2001) 69
20. Clara-Sosa A., Pérez L., Sánchez M., Melgar-Fernández R., Juaristi E., Quintero L., and Anaya de Parrodi C. Tetrahedron 60 (2004) 12147
21. For previous asymmetric syntheses of (R)- and/or (S)-AP-3 and (R)- or (S)-AP-4, see:
22. Villanueva J.M., Collignon N., Guy A., and Savignac P. Tetrahedron 39 (1983) 1299
23. Smith E.C.R., McQuaid L.A., Paschal J.W., and DeHoniesto J. J. Org. Chem. 55 (1990) 4472
24. Soloshonok V.A., Belokon Y.N., Kuzmina N.A., Maleev V.I., Svistunova N.Y., Solodenko V.A., and Kukhar V.P. J. Chem. Soc., Perkin Trans. 1 (1992) 1525
25. Yokomatsu T., Sato M., and Shibuya S. Tetrahedron: Asymmetry 7 (1996) 2743
26. Lohse P.A., and Felber R. Tetrahedron Lett. 39 (1998) 2067
27. Minowa N., Hirayama M., and Fukatsu S. Tetrahedron Lett. 25 (1984) 1147
28. Zeiss H.-J. Tetrahedron 48 (1992) 8263
29. Gage J.R., and Evans D.A. Org. Synth. 68 (1990) 83
30. Janecki T., and Bodalski R. Synthesis (1989) 506
31. Erdik E., and Ay M. Chem. Rev. 89 (1989) 1947
32. Evans D.A., Britton T.C., Ellman J.A., and Dorow R.L. J. Am. Chem. Soc. 112 (1990) 4011
33. Evans D.A., Bartroli J., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127
34. Evans D.A., Takacs J.M., McGee L.R., Ennis M.D., Mathre D.J., and Bartroli J. Pure Appl. Chem. 53 (1981) 1109
35. Evans D.A. Aldrichimica Acta 15 (1982) 23
36. Evans D.A., Nelson J.V., and Taber T.R. Top. Stereochem. 13 (1982) 1
37. 17 shows that dextrorotatory AP-3 corresponds to the (R)-enantiomer.
38. See, for example:
39. Juaristi E. Introduction to Stereochemistry and Conformational Analysis (1991), Wiley, New York, NY
40. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compounds (1994), Wiley, New York, NY
41. Brown H.C., Kramer G.W., Levy A.B., and Midland M.M. Organic Synthesis via Boranes (1975), Wiley, New York, NY pp 12-15
42. Juaristi E., Martínez-Richa A., García-Rivera A., and Cruz-Sánchez J.S. J. Org. Chem. 48 (1983) 2603
43. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923