Stereoselective synthesis of six stereoisomers of inherently chiral methoxy-propoxy-butoxy-methoxycarbonylmethoxy-tert-butylcalix[4]arene

All six possible stereoisomers of calix[4]arenes with four different substituents on the lower rim of the macrocycle have been synthesized by stepwise alkylation of the hydroxyl groups of tert-butylcalix[4]arene using (R)- or (S)-1-phenylethylamide groups as chiral auxiliaries. They form three enantiomeric pairs, as confirmed by the values of their specific rotation.