High-performance liquid chromatographic separation of enantiomers and diastereomers of 2-methylcyclohexanone thiosemicarbazone, and determination of absolute configuration and configurational stability

Journal of Chromatography A

Volumn 1172, Issue 2, 2007, Pages 160-169

  Cirilli, R ^a   Ferretti, R ^a   La Torre, F ^a   Secci, D ^b   Bolasco, A ^b   Carradori, S ^b   Pierini, M ^b  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Ab initio calculations; Absolute configuration; Chiral separation; Chiral synthone; Chiralpak IA; Deracemization; E Z isomerization; Enantiomerization

Indexed keywords

CHIRAL SYNTHONE; DERACEMIZATION; E-Z ISOMERIZATION; ENANTIOMERIZATION;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYSACCHARIDES; SEPARATION; STABILITY CRITERIA; STEREOCHEMISTRY;

ENANTIOMERS;

2 METHYLCYCLOHEXANONE THIOSEMICARBAZONE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CIRCULAR DICHROISM; DIASTEREOISOMER; DRUG STRUCTURE; ENANTIOMER; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; COMPUTATIONAL BIOLOGY; CYCLOHEXANONES; ETHANOL; METHANOL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THIOSEMICARBAZONES;

EID: 35648952796     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chroma.2007.10.009     Document Type: Article

References (33)

1. Wang M., Wang L.F., Li Y.Z., Li Q.X., Xu Z.D., and Qu D.M. Trans. Met. Chem. 26 (2001) 307
2. Yadav L.D.S., and Singh S. Indian J. Chem. 40B (2001) 440
3. Liu M.C., Lin T.S., Cory J.G., Cory A.H., and Sartorelli A.C. J. Med. Chem. 39 (1996) 2586
4. Quiroga A.G., Perez J.M., Lopez-Solera I., Masaguer J.R., Luque A., Roman P., Edwards A., Alonso C., and Navarro-Ranninger C. J. Med. Chem. 41 (1998) 1399
5. Belicchi-Ferrari M., Bisceglie F., Casoli C., Durot S., Morgenstern-Badarau I., Pelosi G., Pilotti E., Pinelli S., and Tarasconi P. J. Med. Chem. 48 (2005) 1671
6. Saloutina L.V., Zapevalov A.Ya., Kodess M.I., Saloutin V.I., and Chupakhin O.N. Russ. J. Org. Chem. 37 (2001) 1522
7. Somogyi L. Liebigs Ann. Chem. (1991) 1267
8. Chimenti F., Maccioni E., Secci D., Bolasco A., Chimenti P., Granese A., Befani O., Turini P., Alcaro S., Ortuso F., Cardia M.C., and Distinto S. J. Med. Chem. 50 (2007) 707
9. Meyers A.I., Williams D.R., Erickson G.W., White S., and Druelinger M. J. Am. Chem. Soc. 103 (1981) 3081
10. Komrlj J., Weigel L.O., Evans D.A., Downey C.W., and Wu J. J. Am. Chem. Soc. 125 (2003) 3208
11. Sakai T., Matsuda A., Tanaka Y., Korenaga T., and Ema T. Tetrahedron: Asymmetr. 15 (2004) 1929
12. Stewart J.D., Reed K.W., Zhu J., Chen G., and Kayser M.M. J. Org. Chem. 61 (1996) 7652
13. Trapp O., Schoetz G., and Schurig V. Chirality 13 (2001) 403
14. Mannschreck A., Zinner H., and Pustet N. Chimia 43 (1989) 165
15. Villani C., and Pirkle W.H. Tetrahedron: Asymmetr. 6 (1995) 1
16. Gasparrini F., Pierini M., Villani C., De Maria P., Fontana A., and Ballini R. J. Org. Chem. 68 (2003) 3173
17. D'Acquarica I., Gasparrini F., Pierini M., Villani C., and Zappia G. J. Sep. Sci. 29 (2006) 1508
18. Wolf C. Chem. Soc. Rev. 34 (2005) 595
19. Mariott P., Trapp O., Shellie R., and Schurig V. J. Chromatogr. A 919 (2001) 115
20. Trapp O., Caccamese S., Schmidt C., Böhmer V., and Schurig V. Tetrahedron: Asymmetr. 12 (2001) 1395
21. Ceccacci F., Mancini G., Mencarelli P., and Villani C. Tetrahedron: Asymmetr. 14 (2003) 3117
22. Cabrera K., Jung M., Fluck M., and Schurig V. J. Chromatogr. A 731 (1996) 315
23. Francotte E.R. J. Chromatogr. A 906 (2001) 379
24. La Torre F., Cirilli R., Ferretti R., Gallinella B., Costi R., and Di Santo R. Chirality 15 (2003) 429
25. Wolf C., König W.A., and Roussel C. Chirality 7 (1995) 610
26. Lorenz K., Yashima E., and Okamoto Y. Angew. Chem., Int. Ed. 37 (1998) 1922
27. Zhang T., Schaeffer M., and Franco P. J. Chromatogr. A 1083 (2005) 96
28. Cirilli R., Orlando V., Ferretti R., Turchetto L., Silvestri R., De Martino G., and La Torre F. Chirality 18 (2006) 621
29. Cirilli R., Ferretti R., Gallinella B., La Torre F., Mai A., and Rotili D. J. Sep. Sci. 29 (2006) 1399
30. Cirilli R., Simonelli A., Ferretti R., Bolasco A., Chimenti P., Secci D., Maccioni E., and La Torre F. J. Chromatogr. A 1101 (2006) 198
31. Zhang T., Kientzy C., Franco P., Ohnishi A., Kagamiharb Y., and Kurosawa H. J. Chromatogr. A 1075 (2005) 65
32. Wellman K.M., Briggs W.S., and Djerassi C. J. Am. Chem. Soc. 87 (1965) 73
33. D.A. Lightner, J.E. Gurst, Organic Conformational Analysis and Stereochemistry from Circular Dichroism Spectroscopy, Wiley-VCH (Chapters II, IV and V).