As an alternative to the classical, shape-based catalyst frameworks that rely on steric destabilization of competing pathways to induce enantioselectivity (Figure , left), substantial effort has been directed over the past several years toward the development of smallmolecule catalysts that achieve enantiocontrol via networks of attractive noncovalent interactions. 8 Noting that charge separation is an embedded feature in all polar reaction mechanisms, we considered whether chiral catalysts capable of stabilizing specific spatial arrangements of charge in selectivity-determining transition states might enable enantioinduction via attractive interactions that are relatively insensitive to perturbations in the steric or even functional features of the reacting partners (Figure , right). Asymmetric recognition of the electrostatic features of transition states could thus give rise to catalysts that display broad scope across different classes of reactions proceeding through similar polar mechanisms.