Two practical methods for highly stereoselective synthesis of (Z)-2-acylamido-4-phenylcrotonates 2a~b have been developed. The key step in the first route was how to control the acid-catalyzed isomerization of condensation mixtures of α-keto ester 5 with carbomite. In the second route the key step was reduction of oxime 8, derived from α-keto ester 5, with iron powder in the presence of acetic anhydride. Two practical methods for highly stereoselective synthesis of (Z) -2-acylamido-4-phenylcrotonates 2a-b have been developed. The key step in the first route was how to control the acid-catalyzed isomerization of the condensation of α-keto esters 5 with carbomite. In the second route the key step was reduction of oxime 8, derived from α-keto ester 5, with iron powder in the presence of acetic anhydride.