The stereoselective allylation of imines and related compounds is one of the most effective methods for the introduction of an amino group into carbon skeletons. Moreover, by extending the process to other C=N functionalities such as oximes, hydrazones, nitrones and iminium ions, a variety of nitrogen-containing functional groups can be prepared with the concomitant introduction of the allyl moiety. In several instances it is possible to achieve a complete stereocontrol by using different organometallic reagents. In other cases, either the protective group tuning or the reaction time is crucial for the stereoselectivity of the reaction. This review covers the evolution of stereoselective allylation of imines and related compounds, including oximes, hydrazones, nitrones and iminium ions, from the use of allylic organometallic reagents over chiral substrates up to the recent development of enantioselective methods.