Enantioselective separation of cyclic chiral ketones and their corresponding diastereomeric alcohols by HPLC on chiral and chiral/chiral coupled stationary phases

Chirality

Volumn 8, Issue 8, 1996, Pages 551-555

  Johnson, Dean V ^a   Wainer, Irving W ^a,b  

^a MCGILL UNIVERSITY   (Canada)

^b MONTREAL GENERAL HOSPITAL   (Canada)

Author keywords

amylose tris 3,5 dimethylphenyl carbamate CSP (AD CSP); cellulose tris 3,5 dimethylphenyl carbamate CSP ODH CSP ; coupled column chromatography; enantioselective HPLC

Indexed keywords

AMYLOSE TRIS 3,5 DIMETHYLPHENYLCARBAMATE; CELLULOSE TRIS 3,5 DIMETHYLPHENYLCARBAMATE; KETONE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHIRALITY; COUPLING FACTOR; ENANTIOMER; ENZYME MECHANISM; ENZYME SUBSTRATE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KETOGENESIS; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030455267     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:8<551::AID-CHIR3>3.0.CO;2-C     Document Type: Article

References (10)

1. König, W.A. The direct resolution of enantiomeric drugs by chiral-phase gas chromatography. In: Drug Stereochemistry, Analytical Methods and Pharmacology, 2nd ed. Wainer, I.W., ed. New York: Marcel Dekker, Inc., 1993:107-137.
2. Schurig, V., Jung. M. Enantiomer separation on dissolved cyclodextrin derivatives by high-resolution gas chromatography: Thermodynamic data of chiral recognition. In: Recent Advances in Chiral Separations. Stevenson, D. and Wilson, I.D., eds. New York: Plenum Press, 1991:117-133.
3. Anon. Chiraldex™ Capillary GC Columns: A Guide to Using Cyclodextrin Bonded Phases for Gas Chromatography. Whippany, NJ: Advanced Separations Technologies, Inc., 1990.
4. Francotte, E., Junker-Buchhrit, A. Preparative chromatographic separation of enantiomers. J. Chromatogr. 576:1-45, 1992.
5. Okamoto, Y., Kaida, Y., Aburatani, R., Hatada, K. Chromatographic optical resolution on polysaccharide carbamate phases. In: Chiral Separations by Liquid Chromatography. Ahuja, S., ed. Washington, DC: American Chemical Society, 1991:101-113.
6. Hollenhorst, Th., Blaschke, G. Direct separation of the enantiomers of propafenone, diprafenone and their major metabolites by high-performance liquid chromatography on modified cellulose and amylose chiral stationary phases. J. Chromatogr. 585:329-332, 1991.
7. Furniss, B.S., Hannaford, A.J., Smith, P.W.G., Tanchel, A.R. Vogel's Textbook of Practical Organic Chemistry. New York: John Wiley and Sons, 1989:519.
8. Mancuso, A.J., Huang, S.-L., Swern, D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride. J. Org. Chem. 43:2480-2482. 1978.
9. Hanschke, E. Zur Kenntnis der Prinsschen Reaktion III. Mitteil.: Über die Reaktion von Allylcarbinol mit Aldehyden und Ketonen. Chem. Ber. 88:1053-1061, 1955.
10. Haslegrave, J.A., Jones, J.B. Enzymes in organic synthesis. 25. Heterocyclic ketones as substrates of horse liver alcohol dehydrogenase. Highly stereoselective reductions of 2-substituted tetrahydropyran-4-ones. J. Am. Chem. Soc. 104:4666-4671, 1982.