Enantiodivergent approach to D-and L-secondary N-hydroxy-R-amino acids by using N-benzyl-2, 3-O-isopropylidene-dglyceraldehyde nitrone as an effective N-hydroxyglycine cation equivalent

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2371-2374

  Merino, Pedro ^a   Castillo, Elena ^a   Franco, Santiago ^a   Merchan, Francisco L ^a   Tejero, Tomas ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CATION; GLYCINE DERIVATIVE; N BENZYL 2,3 O ISOPROPYLIDENE DEXTRO GLYCERALDEHYDE NITRONE; N HYDROXY ALPHA AMINO ACID DERIVATIVE; N HYDROXYGLYCINE; NITRONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 85034386795     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo971913n     Document Type: Article

References (33)

1. Williams, R. M. Synthesis of Optically Active R-Amino Acids; Pergamon Press: Oxford, 1989
2. Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
3. Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264
4. Ojima, I. Acc. Chem. Res. 1995, 28, 383-389.
5. Oppolzer, W. A.; Tamura, O. Tetrahedron Lett. 1990, 31, 991-994.
6. Oppolzer, W.; Tamura, O.; Deerberg. Helv. Chim. Acta 1992, 75, 1965-1978
7. Hanessian, S.; Yang, R.-Y. Synlett 1995, 633-634
8. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273-5276
9. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997-9000.
10. Ottenheijm, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697-707. See also ref 2c and references therein.
11. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero T. J. Org. Chem. 1996, 61, 9028-9032
12. Merino, P.; Anoro, S.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1996, 7, 1887-1890
13. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. J. Org. Chem. 1997, 62, 5497-5507
14. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816
15. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 2381-2401.
16. Bailey, P. D.; Clayson, J.; Boa, A. N. Contemp. Org. Chem. 1995, 2, 173-188
17. Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1997, 38, 3385-3386
18. O'Donnel, M. J.; Bennett, W. D. Tetrahedron 1988, 44, 5389-5401
19. Bretschneider, T.; Miltz, W.; Munster, P.; Steglich, W. Tetrahedron 1988, 44, 5403-5414
20. Abood, N. A.; Nosai, R. Tetrahedron Lett. 1994, 35, 3669-3672
21. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422.
22. Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729.
23. Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 3586-3588.
24. Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567-569.
25. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181-186.
26. Medina, E.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 1581-1586
27. Chattopadhyay, A.; Mamdapur, V. R. J. Org. Chem. 1995, 60, 585-587
28. Poch, M.; Alcon, M.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 1993, 34, 7781-7784.
29. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
30. Martin, T.; Rodriguez, C. M.; Martin, V. S. J. Org. Chem. 1996, 61, 6450-6453.
31. Huber, R.; Vasella, A. Helv. Chim. Acta 1987, 70, 1461-1476.
32. Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 3489-3496
33. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537-2550.