Kinetic resolution of rac-phenylalanine by stereoselective complexation to a chiral cobalt complex through pi-pi stacking interaction.

A cobalt(III) complex with chiral ligand, H2cpel (N-carboxymethyl-N-pyridylethyl-l-leucine), was prepared for chiral recognition of amino acids. Through the competitive coordination of racemic phenylalanine to the chiral cobalt complex, Co(cpel)(CO(3)) (1), enantioselective recognition was achieved on the ternary complex, which was determined on the basis of HPLC analysis with a chiral column. The formation rate for the [Co(cpel)(l-phe)] complex (2) was 6-times superior to that of [Co(cpel)(d-phe)] (3). The preferential formation of 2 might be illustrated by the interligand pi-pi stacking interaction. Crystal structural analysis for 2 and 3 revealed that aromatic rings, pyridine ring of CPEL and phenylalanine sidechain, in 2 were very close each other but those in 3 were far apart. Such interligand aromatic interaction in 2 was also examined by the use of (1)H NMR spectra.