The invention belongs to the technical field of catalytic organic synthesis and particularly relates to a method for catalyzing an asymmetric Michael addition reaction and a catalyst. Nitroolefin and1,3-dicarbonyl ketone are taken as raw materials, a calix[4]squaramide-diaminocyclohexane derivative is taken as a catalyst, dichloromethane is taken as a solvent, the Michael addition catalytic reaction is conducted, after the reaction is completed, the solvent is concentrated, and a product is obtained through silica gel column chromatographic separation. The calix[4]squaramide-diaminocyclohexane catalyst is mild in synthetic process condition and high in catalytic efficiency, the good ee value can be obtained through the catalytic reaction under the room temperature condition, and wide application prospects are realized.