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The synthesis of new chiral N,N'-disuccinate ligands (R,R)-8, (R,R)-9, and (S,S)-10 from (5R)- or (SS)-(menthyloxy)-2(5H)-furanone is described. These ligands, after complexation with EuCl3.6H(2)O, are highly suitable as chiral shift reagents for the enantiomeric excess determination of amino acids and alpha-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.

the journal of organic chemistry

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