Asymmetric synthesis of new chiral europium N,N'-disuccinate complexes: Shift reagents for aqueous solutions and application in the enantiomeric excess determination of amino acids

Article abstract of DOI:10.1021/jo00103a044

The synthesis of new chiral N,N'-disuccinate ligands (R,R)-8, (R,R)-9, and (S,S)-10 from (5R)- or (5S)-(menthyloxy)-2(5H)-furanone is described. These ligands, after complexation with EuCl₃·6H₂O, are highly suitable as chiral shift reagents for the enantiomeric excess determination of amino acids and α-alkylated amino acids in aqueous solutions. Resolution experiments using various amino acids and their derivatives and a study of the pH dependency of the induced diastereomeric shift differences are included.