Computational explorations of enantioselective catalytic mechanisms are a common research endeavor often providing insight into the reaction not possible by experiment. Most investigations focus on new reaction and catalyst examples to reveal the noncovalent interactions at the core of enantioinduction with steric and aromatic interactions being the most common types. In contrast to the rapid developments in this area, revealing unique types of noncovalent interactions to be meaningful stereocontrolling elements in asymmetric catalysis is far less common. In this regard, we have recently characterized the iminium and thionium hydrogen bond as an important contact for determining the outcome of enantioselective catalytic reactions. This talk will describe our recent efforts in applying these new reaction models to understand asymmetric catalysis.