We have shown that 1a catalyzes a range of highly enantioselective reactions spanning disparate functional and steric features at the sites of catalyst binding, thereby displaying an impressive level of substrate and reaction generality. Evidence is provided that the reactions share a common basis for enantioinduction that is tied to the ability of 1a to bind dipolar transition states through attractive electrostatic interactions within an asymmetric dipolar active site. To the extent that charge separation through polar mechanisms underlies a significant subset of synthetically important reactions in organic chemistry, we are hopeful that engineering chiral catalysts to recognize charge rather than specific steric or functional features may offer a promising strategy for attaining generality in asymmetric catalysis.