Efficient and stereoselective synthetic routes to enantiomerically pure (2R,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid have been developed using the stereoselective Strecker type reaction of carbonyl compounds derived from appropriately protected D-glyceraldehyde. The stereoselectivity of the cyanide addition was shown to be dependent on the presence of metal complexing agents, which is essential in the case of (2R)-2,3-di-O-benzyl-D-glyceraldehyde. In addition, theoretical calculations to rationalize the stereochemical course of the reaction have been performed. This work was supported by the Direccion General de Investigacion Cientifica y Tecnica, project number PB94-0578. Peer reviewed