Synthesis of optically pure calix[4]arenes derived from Evans oxazolidinone and/or pyranose

Abstract

Eight new optically pure calixarene derivatives, in which their lower rims were substituted with Evans oxazolidinone or pyranose moieties, are described. All macrocycles were fully characterized by NMR spectroscopy, optical rotation, and elemental analysis. The introduction of chiral auxiliaries reduced the symmetry of the macrocycle as observed by NMR. Stereospecific alkylation on the Evans oxazolidinone moiety allowed the asymmetric introduction of a methyl substituent near a phenolic position of the macrocycle.