Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3.
The (13)C NMR behaviour of 21 p-menthanic terpene bearing an oxygenated function (alcohol, ketone, acetate) was examined in the presence of a chiral lanthanide shift reagent (Yb(hfc)(3)). For each monocyclic compound, we measured the lanthanide-induced shift (LIS) on the signals of the carbons and the splitting of signals allowing the enantiomeric differentiation. Some general features were found about their LIS behaviour: experimental data establishing distinct patterns for carvomenthone-like compounds and menthone-like compounds. The enantiomeric splitting was observed for the majority of signals in the spectrum of each compound. In the case of alcohols and acetates, the influence of the relative stereochemistry (cis vs trans) of isopropyl(ene) and the binding function was discussed.
Lanfranchi
Don Antoine
DA
Université de Corse-CRNS, UMR SPE 6134, Equipe Chimie et Biomasse, Route des Sanguinaires, 20000 Ajaccio, France.
Blanc
Marie-Cécile
MC
Vellutini
Muriel
M
Bradesi
Pascale
P
Casanova
Joseph
J
Tomi
Félix
F
D000085:Acetates; D000438:Alcohols; D002247:Carbon Isotopes; D028581:Lanthanoid Series Elements; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008610:Menthol / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*; D015018:Ytterbium
D000085:Acetates; D000438:Alcohols; D002247:Carbon Isotopes; D028581:Lanthanoid Series Elements; D013729:Terpenes; D008610:Menthol; C019466:menthone; D015018:Ytterbium