(S, S)-pseudoephedrine has proved to be an excellent chiral auxiliary for performing stereocontrolled electrophilic additions on enolates, with an extensive rank of electrophiles.  The use of nitrogen reagents, aldehydes, imines and aziridines as electrophiles has allowed to introduce functionality at α-, β- and γ–positions of the amide substrate.  The diastereoselectivity of the addition reaction was controlled by blocking of one of the enolate and reagent faces.  The so-formed amides were transformed into other valuable chiral nonracemic synthons and heterocyclic compounds.