Enantioselective Synthesis of Fully Protected anti 3-Amino-2-Hydroxy Butyrates

Article abstract of DOI:10.1016/0957-4166(95)00309-D

An efficient enantioselective synthesis of fully protected anti 3-amino-2-hydroxybutyrates has been developed.Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-butanediol, after a change in the nitrogen protecting group, the primary alcohol was protected by regioselective reduction of the corresponding p-methoxybenzylidene acetal.Formation of the oxazolidine and deprotection of the primary alcohol followed by oxidation afforded protected α-hydroxy-β-amino acids in good yield.Since the source of asymmetry is a catalytic Sharpless epoxidation, both enantiomeric series are available and the methodology developed here is expected to be of broad applicability.