An inherently chiral calix[4]crown carboxylic acid in the 1,2-alternate conformation

For better understanding of the structure/property relationship of inherently chiral calixarenes in the 1,2-alternate conformation, we designed and synthesized an inherently chiral calix[4]crown-4 carboxylic acid 1,2-alternate conformer. Resolution of the racemates was effected by condensation with (S)-BINOL as a chiral auxiliary and separation of the resultant diastereomers via preparative TLC plates, followed by hydrolysis of the isolated diastereomers to afford enantiopure antipodes of the title compound. Preliminary property study revealed that the title compound has the ability to enantioselectively discriminate 2-phenylglycinol by 1H NMR spectroscopy.