Ligand Exchange Chromatography of Amino Alcohols. Use of Schiff Bases in Enantiomer Resolution

Article abstract of DOI:10.1021/ja00337a015

A new method for enantiomeric resolution of primary amino alcohols by HPLC is described involving derivatization to the salicylaldehyde Schiff base followed by ligand exchange chromatography (LEC) with chiral L-proline-bonded stationary phases.All of the α-amino alcohols with a hydroxyl substituent on the asymmetric carbon examined were resolved, including catecholamines and other β-hydroxyphenethylamines.The copper(II) ion employed in LEC serves to stabilize the Schiff base, whereas the derivative permits complexation in a manner favorable for resolution and enhanced detection.A possible structure for the mixed complex responsible for separation is suggested.From this structure, a correlation between elution order and configuration is proposed.