Effect of the presence of a free hydroxyl group on the enantiodiscrimination properties of cholic acid based CSPs bearing 2-naphthylcarbamate and 3,5-dinitrophenylcarbamate moieties in the HPLC resolution of racemic compounds

Tetrahedron Asymmetry

Volumn 16, Issue 23, 2005, Pages 3820-3828

  Iuliano, Anna ^a   Ruffini, Andrea ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHYLCARBAMATE; 3,5 DINITROPHENYLCARBAMATE; CARBAMIC ACID DERIVATIVE; CHOLIC ACID; HYDROXYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DERIVATIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 28644447011     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.10.036     Document Type: Article

References (19)

1. W.H. Pirkle, and T.C. Pochapsky Chem. Rev. 89 1989 347 362
2. F. Gasparrini, D. Misiti, and C. Villani J. Chromatogr. A 906 2001 35 50
3. C.J. Welch J. Chromatogr. A 666 1994 3
4. A. Iuliano, E. Attolino, and P. Salvadori Eur. J. Org. Chem. 2001 3523 3529
5. A. Iuliano, E. Attolino, and P. Salvadori Tetrahedron: Asymmetry 13 2002 1805 1815
6. A. Iuliano, and C. Lecci Tetrahedron: Asymmetry 14 2003 1345
7. A. Iuliano, and G. Félix J. Chromatogr. A 1031 2004 187
8. A. Iuliano, P. Salvadori, and G. Félix Tetrahedron: Asymmetry 10 1999 3353 3364
9. A. Iuliano, I. Pieraccini, G. Félix, and P. Salvadori Tetrahedron: Asymmetry 13 2002 1265 1275
10. L.F. Fieser, and S. Rajagopalan J. Am. Chem. Soc. 71 1949 3935
11. L. D'Souza, and U. Maitra J. Org. Chem. 61 1996 9494 9502
12. A.M. Bellini, M.P. Quaglio, M. Guarneri, and G. Cavazzini Eur. J. Med. Chem.-Chim. Ther. 18 1983 185
13. R. Grand, and T. Reichstein Helv. Chim. Acta 28 1945 344
14. C. Rosini, C. Bertucci, D. Pini, P. Altemura, and P. Salvadori Tetrahedron Lett. 26 1985 3361 3364
15. A. Iuliano, and P. Scafato Tetrahedron: Asymmetry 14 2003 611
16. G. Alagona, C. Ghio, A. Iuliano, S. Monti, I. Pieraccini, and P. Salvadori J. Org. Chem. 68 2003 3145
17. L. Vaton-Chanvrier, H. Oulyadi, G. Coquerel, Y. Combret, and J.C. Combret Chirality 13 2001 668
18. W.H. Pirkle, and C.J. Welch Tetrahedron: Asymmetry 5 1994 777 780
19. 13 and not a hypothesis of an enantiorecognition mechanism, which deserves further studies to be elucidated: work is currently in progress on this topic.