Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source

Article abstract of DOI:10.1016/0957-4166(96)00037-7

A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure α-hydroxy-β-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S,3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.