Design and Synthesis of Chiral Stationary Phase Derived from (S)-[10]Paracyclophane-13-carboxylic Acid for the HPLC Separation of Enantiomers

Homochiral (S)-[10]paracyclophane-13-carboxylic acid ((S)-1) could conveniently be obtained on a preparative scale via fractional crystallization of the (S)-1-phenylethylamide diastereomers. (S)-1 was used for the first time as a stereodifferentiating element with planar chirality for a new chiral stationary phase (CSP) for HPLC. The CSP, which was prepared by bonding (S)-1 to γ-aminopropylsilanized silica gel via amide linkage, recognized a wide range of enantiomers by HPLC.