Synthesis of meso-2,4-diaminoglutaric acid

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1555-1558

  Avenoza, Alberto ^a   Cativiela, Carlos ^b   Peregrina, Jesús M ^a   Zurbano, María M ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIAMINOGLUTARIC ACID; ALDEHYDE; GLUTARIC ACID DERIVATIVE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HYDROGENATION; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0029935978     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00179-6     Document Type: Article

References (39)

1. For leading recent references see: (a) Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699.
2. (b) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 1, 113.
3. (c) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244.
4. (d) Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303.
5. (e) Mendel, D.; Ellman, J.; Schultz, P. G. J. Am. Chem. Soc. 1993, 115, 4359.
6. (f) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
7. (a) Williams, R. M. ; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976.
8. (b) Williams, R. M. ; Yuan, Ch. J. Org. Chem. 1992, 57, 6519.
9. (c) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727.
10. (d) Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H.-P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865.
11. (e) Baldwin, J. E.; Lee, V.; Schofield, C. J. Synlett 1992, 249.
12. (f) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147.
13. (g) Mueller, R.; Revesz, L. Tetrahedron Lett. 1994, 35, 4091.
14. (a) Schöllkopf, U.; Busse, U.; Lonsky, R.; Hinrichs, R. Liebigs. Ann. Chem. 1986, 2150.
15. (b) Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs. Ann. Chem. 1989, 1215.
16. (a) Belokon, J. N.; Chenroglazova, N. I.; Batsanov, A. S.; Carbalinskaya, N. S.; Bakhmutov, V. I.; Struchkov, Y. T.; Belikov, V. M. Izv. Akad. Nauk. SSSR Ser. Khim. 1987, 852.
17. (b) Mulzer, J. A.; Schröder, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737.
18. (a) Garner, P.; Park, J.-M. J. Org. Chem. 1987, 52, 2361.
19. (b) Garner, P.; Park, J.-M. Org. Synth. 1991, 70, 18.
20. (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53.
21. (b) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159.
22. (c) Schmidt, U.; Lieberknecht, A.; Kazmaier, U.; Griesser, H.; Jung, G.; Metzger, J. Synthesis 1991, 49.
23. (d) Schmidt, U.; Lieberknecht, A.; Meyer, R.; Leitenberger, V.; Stäbler, F. Synthesis 1991, 409.
24. (a) Herbst, R. M.; Shemin, D. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p11.
25. (b) Hanby, W. E.; Waley, S. G.; Watson, J. J. Chem. Soc. 1950, 3239.
26. (c) Easton, C. J.; Scharfbillig, I. M. J. Org. Chem. 1990, 55, 384.
27. (d) Kober, R.; Steglich, W. Liebigs Ann. Chem. 1983, 599.
28. 1H-NMR signals corresponding to the allylic protons: (Z): δ 4.65(m, 1H); (E): δ 5.25(m, 1H).
29. (a) Keah, H. H.; Rae, I. D. Aust. J. Chem. 1993, 46, 1413.
30. (b) Pihlaja, K.; Kleinpeter, E. Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis VCH: New York 1994.
31. (c) Breitmaier, E. Structure Elucidation by NMR in Organic Chemistry Wiley: New York 1993.
32. Severn, W. B.; Richards, J. C. J. Am. Chem. Soc. 1993, 115, 1114.
33. Diastereofacial selectivity was determined by HPLC using a 40:60 hexane:tert-butylmethyl ether mixture as the mobile phase and a flow rate of 2.0 mL/min. Retention times: 4 = 13.70 min, 5 = 11.30 min, 2 = 7.26 min.
34. Further studies are in progress in order to explain the stereochemical outcome of the hydrogenation reaction.
35. Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39.
36. Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196.
37. 2); 49.5(CH); 170.3(COO).
38. Blake, J.; Folden, L. Biochem. J. 1964, 92, 136.
39. Wiesom, H.; Canuam, R. J. Biol. Chem. 1937, 119, 309.