Synthesis of inherently chiral azacalix[4]arenes and diazadioxacalix[4]arenes.

Described are nucleophilic aromatic substitution reactions for the synthesis of inherently chiral azacalix[4]arenes and diazadioxacalix[4]arenes comprised of two or three different aromatic monomers. A variety of functional groups are tolerated at the 2-, 4-, and 5-positions on the nucleophilic-component monomers; reactions are run under ambient atmosphere; and the macrocycles are constructed without isolation of intermediate linear species.