Enantiomeric enrichment of non-racemic mixtures of binaphthol with non- chiral packings

Chirality

Volumn 8, Issue 3, 1996, Pages 234-243

  Nicoud, Roger Marc ^a   Jaubert, Jean Noël ^a   Rupprecht, Isabell ^a   Kinkel, Joachim ^b  

^a UNIVERSITÉ DE LORRAINE   (France)

^b Division Laboratory Products   (Germany)

Author keywords

binaphtol; enantiomeric; non racemic mixtures

Indexed keywords

NAPHTHOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CHROMATOGRAPHY; ENANTIOMER; MATHEMATICAL MODEL; PRIORITY JOURNAL;

EID: 0029783236     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:3<234::AID-CHIR2>3.0.CO;2-H     Document Type: Article

References (21)

1. 14C-labeled nicotine: separation of enantiomers in a totally achiral system. J. Chromatogr. 281:17-33, 1983.
2. Charles, R., Gil-Av, E. Self-amplification of optical activity by chromatography on an achiral adsorbent. J. Chromatogr. 298:516-520, 1984.
3. Tsai, W.-L, Hermann, K., Rohde, B., Dreiding, A.S. Enantiomer-differentiation induced by an enantiomeric excess during chromatography with achiral phases. Helvetica Chimica Acta, 68:2238-2243, 1985.
4. Dobashi, A., Motoyama,Y., Kinoshita, K., Hara, S., Fukasaku, N. Self-induced chiral recognition in the association of enantiomeric mixtures on silica gel chromatography. Anal. Chem. 59(17):2209-2211, 1987.
5. Matusch, R., Coors, C. Chromatographic separation of the excess enantiomer under achiral conditions. Angew. Chem. Int. Ed. Engl., 28(5):626-627, 1989.
6. Diter, P., Taudien, S., Samuel, O., Kagan, H.B. Enantiomeric enrichment of sulfoxides by preparative flash chromatography on an achiral phase. J. Org. Chem. Eng. 59(2):370-373, 1994.
7. Williams, T., Pitcher, R.G., Bommer, P., Gutzwiller, J., Uskokovic, M. Diastereomeric solute-solute interactions of enantiomers in achiral solvents. Non- equivalence of the nuclear magnetic resonance spectra of racemic and optically active dihydroquinine. J. Amer. Chem. Soc. 91(7):1871-1872, 1969.
8. Cung, M.T., Marraud, M., Neel, J. Etude expérimentale de l'auto-association des molécules modèles dipeptidiques. Association Stéréosélective des molécules enantiomères. Biopolymers 15:2081-2095, 1976.
9. Cung, M.T., Marraud, M., Neel, J. Etude expérimentale de l'auto-association des molécules modèles dipeptidiques. Influence de la dimérisation stéréosélective sur les spectres de résonance magnétique protonique. Biopolymers 16:715-729, 1977.
10. Cung, M.T., Marraud, M., Neel, J. Experimental study on aggregation of model dipeptide molecules. Stéréosélective association of leucine dipeptides. Biopolymers 17:1149-1173, 1978.
11. Cung, M.T., Marraud, M., Neel, J. Utilisation de la résonance magnétique nucléaire pour évaluer le degré de pureté optique de certains dérivés peptidiques dont la molécule ne contient qu'un seul centre chiral. C.R. Acad. Sc. Paris, t.281, série C, 691-694, 1975.
12. Cung, M.T., Marraud, M. Experimental study on aggregation of model monopeptide molecules: a model for peptide β-structures? Int. J. Biol. Macromol. 6:13-20, 1984.
13. Cung, M.T., Marraud, M. Experimental study of aggregation of model monopeptide molecules: modeling of peptide β-structure association modes. Journal de chimie physique 82(1):33-42, 1985.
14. Kabachnik, M.I., Mastryukova, T.A., Fedin, E.I., Vaisberg, M.S., Morozov, LL, Petrovsky, P.V., Shipov, A.E. An NMR study of optical isomers in solution. Tetrahedron 32:1719-1728, 1976.
15. Kabachnik, M.I., Mastryukova, T.A., Fedin, E.I., Vaisberg, M.S., Morozov, LL, Petrovsky, P.V., Shipov, A.E. Optical isomers in solution investigated by nuclear magnetic resonance. Russian Chemical Reviews 47(9):821, 1978.
16. Davankov, VA, Meyer, V.R., Rais, M. A vivid model illustrating chiral recognition induced by achiral structures. Chirality 2:208-210, 1990.
17. Coors, C. "Chromatographische Gewinnung Von Enantiomeren An Chiralen und Achiralen Phasen". Ph.D. Dissertation. The German University of Marburg, 1988.
18. Jung, M., Schurig, V. Computer simulation of three scenarios for the separation of non-racemic mixtures by chromatography on achiral stationary phases. J. Chromatogr. 605:161-166, 1992.
19. Gil-Av, E., Schurig, V. Resolution of non-racemic mixtures in achiral chromatographic systems: A model for the enantioselective effects observed. J. Chromatogr. A 666:519-525, 1994.
20. Davankov, VA Separation of enantiomeric compounds using chiral HPLC systems. A brief review of general principles, advances, and development trends. Chromatographia 27(9/10):475-482, 1989.
21. Jönsson, Lövkvist. Determination of adsorption isotherms for chromatographic measurements using the peak maxima method. J. Chromatogr. 408:1-7, 1987.