Chiral capillary electrophoresis applied to the determination of phenylglycidol enantiomers obtained from cinnamyl alcohol by asymmetric epoxidation using new titanium(IV) alkoxide compounds as catalysts.
A capillary electrophoresis method for the simultaneous determination of phenylglycidol enantiomers in the presence of an excess of cinnamyl alcohol was developed. The effects of the nature, pH and concentration of the buffer, the nature and concentration of chiral selector, the addition of methanol or acetonitrile, and the capillary temperature on the chiral resolution of phenylglycidol enantiomers were studied. Separations were achieved using 20 mM succinylated beta-cyclodextrin dissolved in a 10 mM borate buffer (pH 10.0). Chiral resolution for the phenylglycidol enantiomers in the optimized electrophoretic conditions was higher than 2.0 with an analysis time less than 7 min. The method developed was validated in terms of selectivity, linearity, precision (instrumental repeatability, method repeatability, intermediate precision), the limits of detection and quantitation, and accuracy. Limits of detection of 6.5 mg/L and 8.3 mg/L for (2S,3S)-(-)-3-phenylglycidol ((S,S)-PG) and (2R,3R)-(+)-3-phenylglycidol ((R,R)-PG), respectively, were obtained. The method was applied to study the asymmetric epoxidation of cinnamyl alcohol with titanium(IV) alkoxide compounds as catalysts in order to evaluate their catalytic activity and stereoselectivity of the epoxidation processes.
Morante-Zarcero
Sonia
S
Departamento de Química Analítica, Facultad de Química, Universidad de Alcalá, Alcalá de Henares (Madrid), Spain.
Crego
Antonio L
AL
Sierra
Isabel
I
Fajardo
Mariano
M
Marina
M Luisa
ML
D002021:Buffers; D002384:Catalysis; D003505:Cyclodextrins; D019075:Electrophoresis, Capillary / Q000379:methods* / Q000706:statistics & numerical data; D004852:Epoxy Compounds / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism; D014025:Titanium
D002021:Buffers; D003505:Cyclodextrins; D004852:Epoxy Compounds; D020005:Propanols; D014025:Titanium; C020722:cinnamyl alcohol