A cumene solution of alpha -stannyl benzyl phenyl sulfide was treated with n-BuLi and bis(oxazoline)-Pr-i: at -78 degreesC and subsequently with benzophenone to give the product with 99% ee. We confirmed that the reaction of alpha -lithio benzyl phenyl sulfide proceeds through a dynamic kinetic resolution pathway. The enantioselective reactions of alpha -lithio benzyl 2-pyridyl sulfide gave the products with stereochemistry reverse to that obtained in the reaction of benzyl phenyl sulfide. We confirmed that this reaction proceeds through a dynamic thermodynamic resolution pathway in which the reaction with an electrophile proceeds faster than interconversion between the diastereomeric complexes.