1-phenylethyl isocyanate is a powerful reagent for the chiral analysis of secondary alcohols and hydroxy fatty acids with remote stereogenic centres.
1-phenylethyl isocyanate (1-PEIC), a chiral derivatisation reagent for the resolution of secondary alcohols is a powerful tool to determine the configuration and enantiomeric excess of medium- to long-chain secondary alcohols by capillary gas chromatography. The separation of 1-phenylethylcarbamates (1-PECs) of secondary alcohols was systematically evaluated depending on the position of the stereogenic centre in the molecule, namely in alkanols (C(15)-C(18)), alkenols (C(15)-C(18)) and hydroxy fatty acids (C(14)-C(18)). The successful separation of the diastereomeric carbamates of (+/-)-heptadecan-7-ol or (+/-)-12-hydroxyoctadecanoic acid methyl ester by gas liquid chromatography demonstrates the unique separation power for 1-PECs for analytes with remote stereogenic centres. Saturated derivatives showed consistently higher resolution factors than the corresponding unsaturated derivatives.
Habel
Andreas
A
Max Planck Institute for Chemical Ecology, Bioorganic Chemistry, 07745 Jena, Germany.
Spiteller
Dieter
D
Boland
Wilhelm
W
D000438:Alcohols / Q000302:isolation & purification*; D005227:Fatty Acids / Q000302:isolation & purification*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D017953:Isocyanates / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D005227:Fatty Acids; D017953:Isocyanates; C020790:phenylethyl isocyanate