(1S,2R)-N-(3,5-DINITROBENZOYL) NOREPHEDRINE BONDED TO SILICA-GEL AS A CHIRAL STATIONARY PHASE FOR THE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS

A Chiral Stationary Phase (CSP 3) was prepared by connecting (1S, 2R)-N-(3,5-dinitrobenzoyl) norephedrine to a silica support through an ester linkage. CSP 3 was found to show some differences from CSP 1, derived from N-(3,5-dinitrobenzoyl) phenylglycine, in the resolution of N-acyl-1-aryl-1-aminoalkanes. For example, CSP 3 was found to show greater chiral recognition for conformationally rigid analytes than does CSP 1. On the other hand, CSP 1 was found to resolve flexible analytes better than CSP 3. To explain the chiral recognition behavior on CSP 3, the role of the conformational flexibility of CSP 3 in chiral recognition is proposed.