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Abstract: Molecularly imprinted sites on a silica gel (alumina) surface, "footprints", are complementary cavities with Lewis acid sites at their bottoms. These sites exhibit catalytic behaviour with tailored specificities, which distinguish footprints from the imprinted absorption sites in vinyl polymers. Our studies of enantioselective catalysis over chirally imprinted cavities reveal that there are two enantioselective mechanisms. The major mechanism allows a chiral molecule to bind in two postures, which produces low enantioselectivities. Another mechanism is observed for binding over the exclusive cavities that accept only one binding posture of a chiral molecule, which brings highly enantioselective catalysis. Our investigation of these binding postures provides useful information on how to design templates for cavities to provide fine molecular recognition