Enantioselective Robinson-type annulation reaction between β-ketoamide and α,β-unsaturated ketone was developed by utilizing the amino acid derived primary-secondary diamine catalysts. The less reactive acyclic β-ketoamides employed as both electrophile and nucleophile are reported in this asymmetric tandem reaction. A number of chiral cyclohexenone derivatives containing an amide group were obtained in high yields and good selectivities.