A highly trans diastereoselective synthesis of 2,4,5‐trisubstituted oxazoline derivatives is described that proceeds through a palladium‐catalyzed coupling–cyclization reaction of N‐(buta‐2,3‐dienyl)amides with aromatic iodides. The reaction with optically active substrates provides convenient access to highly enantioenriched oxazoline derivatives with excellent 1,2‐induction.