Footprint Catalysis. XI. Molecular Footprint Cavities Imprinted with Chiral Amines and Their Chiral Molecular Recognition

Chiral amines, (R)- and (S)-N-benzyl-α-methylbenzylamine, served as templates in a molecular imprinting we developed. They formed “molecular footprint” cavities on a silica (alumina) gel surface, which showed catalytic activities toward transacylation of benzoic anhydride. The catalyses were susceptible to enantioselective inhibitions by the rebinding of the chiral template amines. This finding proved that the cavities could show chiral recognition through their chirally marked cavity structures.