(1S,2R)-N-(3,5-Dinitrobenzoyl) Norephedrine Bonded to Silica Gel as a Chiral Stationary Phase for the Liquid Chromatographic Separation of Enantiomers

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Abstract
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.