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Enantiomeric differentiation of oxygenated p ‐menthane derivatives by 13 C NMR using Yb(hfc) 3
Author(s) -
Lanfranchi Don Antoine,
Blanc MarieCécile,
Vellutini Muriel,
Bradesi Pascale,
Casanova Joseph,
Tomi Félix
Publication year - 2008
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2330
Subject(s) - chemistry , lanthanide , enantiomer , ketone , enantiomeric excess , reagent , isopropyl , menthone , stereochemistry , diastereomer , carbon 13 nmr , nuclear magnetic resonance spectroscopy , alcohol , terpene , acetophenone , organic chemistry , medicinal chemistry , menthol , enantioselective synthesis , catalysis , ion
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. Copyright © 2008 John Wiley & Sons, Ltd.