Comparison of column performances in direct high‐performance liquid chromatographic enantioseparation of 1‐ or 3‐methyl‐substituted tetrahydroisoquinoline analogs. Application of direct and indirect methods

The enantioseparability of 1‐ or 3‐methyl‐substituted tetrahydroisoquinolines was investigated by direct and indirect high‐performance liquid chromatography. α ‐ and β ‐cyclodextrin‐, macrocyclic glycopeptide‐ and cellulose‐based chiral columns and isothiocyanate‐ and Sanger‐type chiral derivatizing agents (CDAs) were applied to attain satisfactory enantioseparation. Of the chiral columns, β ‐cyclodextrin‐, vancomycin‐ and teicoplanin‐containing macrocyclic glycopeptide‐based columns appeared to be most suitable; of the CDAs, (1 S ,2 R )‐1‐acetoxy‐1‐phenyl‐2‐propyl isothiocyanate was most favorable. The differences between the selectivities of the columns and CDAs were compared and optimized to yield the best resolution. Copyright © 2005 John Wiley & Sons, Ltd.