Diastereoselective Strecker reaction of D-glyceraldehyde derivatives. A novel route to (2S,3S)- and (2R,3S)-2-amino-3,4-dihydroxybutyric acid

Abstract Efficient and stereoselective synthetic routes to enantiomerically pure (2 R ,3 S )- and (2 R ,3 S )-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 (2 R )-2,3-di- O -benzyl- D -glyceraldehyde. In addition, theoretical calculations to rationalize the stereochemical course of the reaction have been performed.