Use of chiral lanthanide shift reagents in the elucidation of NMR signals from enantiomeric mixtures of polycyclic compounds †

Abstract

1 H and 13C NMR is used to study the effects on a set of racemic polycyclic compounds of the application of the chiral shift reagents europium(III) tris[3-(trifluoromethylhydroxymethylene)-(+)-camphorate] and europium(III) tris[3-(heptafluoropropylhydroxymethylene)-(+)-camphorate]. The study compares the chiral shift reagents to find the conditions resulting in optimum enantiomeric (ΔΔδ) and spectral resolution (Δδ). Of the two reagents Eu(hfc)3 proved to be the more efficient. In addition, the effect of the achiral lanthanide shift reagent Eu(fod)3, used in combination with the chiral lanthanide shift reagents, was investigated.