Synthesis and characterization of an inherently chiral calix[6]arene in the 1,4-alternate conformation

An inherently chiral calix[6]arene possessing a C2-symmetric A-B-H substitution pattern was synthesized via a two step process starting from the parent hexa-t-butylcalix[6]arene. The racemic, inherently chiral compound exists as a single isomer with the 1,4-alternate conformation. The inherent chirality was confirmed by treatment of the racemic compound with Pirkle's reagent to form diastereomeric complexes in solution.