Reactions of Amino Acid Decyl Esters with Nucleophiles Catalyzed by Polymer-Supported Amine-Metal Complexes

Article abstract of DOI:10.1246/bcsj.68.1669

The reactions of alanine decyl ester (AlaODc) with nucleophiles were catalyzed by a crosslinked polystyrene-supported ethylenediamine-copper(II) ion complex (Cu en-PS) under toluene/resin two-phase conditions or toluene/ aqueous buffer/resin three-phase conditions.In the two-phase reactions with octylamine, the rate was increased with a decreasing metal content of the resin.The catalytic efficiency was also dependent on other factors, that is, metal ion, ligand structure, and substrate structure.In the three-phase reactions with water, the hydrolysis was very fast when acetate ions were present in the aqueous phase.It has been suggested that the reactions proceed via a substrate-coordinated intermediate complex under both conditions.