Cations and anions are fundamental species whose interactions have been thoroughly studied and widely applied in organic synthesis, particularly to control the selectivity in chemical transformations. Strategies exploiting ion pairing have proven to be applicable to a broad range of reactions that proceed via anionic intermediates and cationic species. Considering the general versatility of ion pairs in constructing well-organized transition structures, we utilized these powerful attractive interactions to construct catalyst structures. This account summarizes the design and applications of ion-paired chiral ligands and chiral 1,2,3-triazolium salts. Ions are fundamental species in organic chemistry; thus, the interactions between cations and anions have been extensively studied and are widely applied in organic synthesis, particularly to control the selectivity of chemical transformations. Considering the general versatility of ion pairs in constructing well-organized transition structures, we utilized these powerful attractive interactions for the construction of catalyst structures.