A mild and efficient method for the asymmetric Michael addition of cyclohexanone to various chalcones is reported. The reusable ionic liquid (IL) [EMIm][Pro] 1 was used as chirality inductor. The products were obtained in moderate to excellent yields and moderate to high enantioselectivities in the presence of co-solvents like methanol. Interestingly, the enantioselectivity in DMSO as co-solvent was found to be inverted. The reaction can be assumed to proceed via intermediate 2.