Doubly diastereoselective 1,3-dipolar cycloadditions of chiral azomethine ylides to cinnamoyl moieties, attached to chiral auxiliaries, were investigated. The resulting trans-3,4-disubstituted pyrrolidines were obtained in diastereomeric ratios of up to 78:22. The influence on this ratio by the constitution of the chiral ylide was found to be rather small.