Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC.

A pair of optically active triptycene derivatives ((,)- and (,)-8) with a distorted cyclic structure were synthesized an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (,)- and (,)-8-based chiral stationary phases (CSPs) were found to be particularly effective in the resolution of axially chiral biaryl compounds. The importance of the distorted cyclic structure present in 8 for chiral recognition was demonstrated by comparisons with the corresponding non-cyclic model compound ((,)-9), which did not display enantioselectivity in the separation of the test racemates.