The present review is mainly focused upon the use of C-substituted oxazolidin-2-ones as chiral auxiliaries in the stereocontrolled C-C and C-X (X = hetero atom) bond formation. The recent progress in the stereoselective alkylation, cycloaddition and aldol reaction, as well as in the 1,4-coniugate addition, in [2+2]-photocycloaddition, in Lewis acid promoted free-radical copolymerization reactions are discussed. Emerging new applications of the oxazolidin-2-one nucleus, such as building blocks in the design and preparation of foldamers or as organocatalyst in enantioselective epoxidation reactions, will be also discussed. © 2007 Bentham Science Publishers Ltd.