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Keywords: Amino acids / Enantioselectivity / Chirality / Molecular recognition / CavitandsTwo new receptors, a cavitand-salen (2) and a uranyl-cavitand-salen (3), for the selective molecular recognition of chiral ammonium ion pairs, where the amino acid is the countercation or counteranion of the ion pair, were designed and synthesized. UV/Vis measurements indicate the formation of 1:1 host-guest complexes with high association constants and good to excellent enantiomeric discriminations.