This paper describes an efficient kinetic resolution of racemic enol ester epoxides via a chiral Lewis acid catalyzed rearrangement. Both enantiomerically enriched enol ester epoxides and alpha-acyloxy ketones can be obtained through this resolution. A positive nonlinear effect is observed in this process. By taking advantage of the mechanistic duality in acid-catalyzed enol ester epoxide rearrangement, we can completely convert a racemic enol ester epoxide into an enantiomerically enriched alpha-acyloxy ketone by treatment with a catalytic amount of a chiral Lewis acid followed by a catalytic amount of an achiral protic acid.