Synthesis of inherently chiral wide rim ABC substituted calix[6]arene derivatives

Abstract

An efficient synthetic route to inherently chiral calix[6]arenes with an ABC substitution pattern at the wide rim and a mesitylenyl unit at the narrow rim in the cone conformation was developed for the first time. Based on the selective formylation and bromination of 1,3,5-bridged calix[6]arene 1, two new inherently chiral calix[6]arene derivatives 4 and 5 have been prepared with moderate yields. The 1H NMR spectra indicate that these inherently chiral compounds adopt a cone conformation and their three different groups at the wide rim can create a chiral environment inside the cavity that maybe sensed by some chiral guests, which has also been confirmed by X-ray crystal structure of 4 and molecular modelling of 5. Complexation studies show that 5 displays exceptional properties for the binding of .