SOLID-LIQUID PHASE TRANSFER CATALYTIC SYNTHESIS OF α-AMINO ACID VIA ALKYLATION AND NUCLEOPHILIC ADDITION OF BENZALDEHYDE IMINES

Article abstract of DOI:10.1016/S0040-4020(01)86041-5

A short, mild and efficient synthetic route of α-amino acid via alkylation, Michael addition and carbonyl addition as well as cycloaddition of aldimines derived from glycine and alanine esters with benzaldehyde under solid-liquid phase transfer catalytic condition has been studied.The key to solid-liquid phase transfer catalyzed reactions is the selection of a base for the various reactants.The yield is dependent on the base used.The results obtained using KOH, K2CO3 and Na2CO3 are discussed.The kinetics of solid-liquid PTC benzylation has been investigated and we propose a possible mechanism of solid-liquid PTC as an interface auto-catalytic procedure.The details of some syntheses of α-amino acids are presented.