Abstract
The 200 MHz 1H NMR spectra of citiolone, 1, have been studied in CDC13 solution at ambient temperatures with the achiral lanthanide shift reagent (LSR) tris (6, 6, 7, 7, 8, 8, 8-heptafluoro-2, 2-dimethyl-3, 5-octanedionato) europium (III), Eu (FOD)3, 2, for spectral simplification, and with the chiral LSR, tris [3-heptafluoropropylhydroxymethylene)-(+)-camphorato] europium (III), Eu (HFC)3, 3. With 3, substantial enantiomeric shift differences were obtained for the H-3, NH and CH3CO resonances, with the H-3 signals essentially baseline resolved and free from overlaps with [3]/[1] molar ratios ca. 0.8–1.0. For the acetyl signal, valley heights as low as 4–5% were achieved between the signals of the antipodes when [3]/[1] ratios ca. 0.7–0.8 were used. These conditions should permit direct determinations of enantiomeric excess of 1.
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