C. Cativiela et al., STEREOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY-BETA-AMINO ACIDS USING D-GLYCERALDEHYDE AS THE HOMOCHIRAL SOURCE, Tetrahedron : asymmetry, 7(2), 1996, pp. 529-536
A systematic study of the diastereoselective addition of methyl organo
metallic compounds to the benzyl imine derived from conveniently prote
cted D-glyceraldehyde in order to develop a new approach to enantiomer
ically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesiu
m bromide addition afforded the corresponding adduct, which can be fur
ther elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with
complete diastereoselectivity.