Stereospecific Synthesis of N--α,β-Didehydroamino Acid Methyl Esters, New Synthons in the Synthesis of α-Amino Acids

Article abstract of DOI:10.1016/S0040-4020(01)80317-3

N--α,β-didehydroamino acid methyl esters 4a-c have been prepared with total geometric selectivity from easily accesible β-hydroxyamino acids through N--β-hydroxyamino acid methyl esters 3a-c as intermediates.The (E)-isomers can be easily converted into the corresponding (Z)-isomers in the presence of a catalytic amount of titanium (IV) chloride. Key words: Stereospecific dehydration, stereoisomers, didehydroamino acids, amino acids, E-Z isomerization