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 (C15–C18), alkenols (C15–C18) and hydroxy fatty acids (C14–C18). 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.