High-performance liquid chromatographic enantioseparation of bicyclic 1,3-amino alcohols.
Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of diendo- and diexo-3-aminobicyclo[2.2.1]heptane-2-methanol and diendo- and diexo-3-amino-bicyclo[2.2.1]hept-5-ene-2-methanol derivatives. Direct separation was carried out on a naphthylethyl carbamate-derivatized beta-cyclodextrin (Cyclobond I 2000 SN) stationary phase, which was used in the polar-organic mode. This allowed the simultaneous separation of stereoisomers of alcohol and ester analogs of the bicyclic 1,3-amino alcohols. Alternatively, the derivatization of amino alcohols on the amino group with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide produced diastereomers which were separable with high resolution (Rs>5-10) on a LiChrospher RP-18 stationary phase. The order of elution of the enantiomers was determined by both direct and indirect methods.
Péter
A
A
Department of Inorganic and Analytical Chemistry, University of Szeged, Hungary. apeter@chem.u-szeged.hu
Kámán
J
J
Fülöp
F
F
van der Eycken
J
J
Armstrong
D W
DW
D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D013237:Stereoisomerism
D000438:Alcohols; D001643:Bridged Bicyclo Compounds