We describe herein a new strategy for the chemoselective synthesis of amides by using a metal catalyzed hydroxy-directed reaction. A hydroxy group located at the beta-position of an ester group promoted the activation of a carbonyl group with a tantalum alkoxide catalyst followed by amidation reactions, leading to a wide variety of beta-hydroxyamides with excellent chemeselectivity. The chemoselective amidation strategy can be extended to the catalytic synthesis of dipeptide derivatives, which remains challenging research subjects in modern organic synthesis.