Calix[4]arenes with Combined Axial Chirality and Inherent Chirality: Synthesis, Absolute Configuration and Chiral Recognition

Calix[4]arene diastereomeric pairs with combined axial chirality and inherent chirality were readily synthesized via monoalkylation of 1,2-substituted calix[4]arene crown-4 incorporating an axially chiral binaphthyl moiety with different electrophiles as a key step. The reaction showed high generality and distinct diastereoselectivity. The easy separation of the diastereomers, the good diastereoselectivity of the reaction, and the poor stereoselectivity of the chiral recognition of diastereomeric pairs were attributed to the remarkable steric effect of the axially chiral binaphthyl moiety. Absolute configurations were determined by X-ray crystallography.