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Enantiomeric differentiation of acyclic terpenes by 13 C NMR spectroscopy using a chiral lanthanide shift reagent
Author(s) -
Blanc MarieCécile,
Bradesi Pascale,
Casanova Joseph
Publication year - 2005
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.1523
Subject(s) - chemistry , lanthanide , enantiomer , reagent , terpene , alcohol , nuclear magnetic resonance spectroscopy , enantiomeric excess , stereochemistry , spectroscopy , organic chemistry , enantioselective synthesis , catalysis , physics , quantum mechanics , ion
The 13 C NMR behaviour of ten acyclic terpene alcohols was examined in the presence of a chiral lanthanide shift reagent (CLSR). For each alcohol, we measured the lanthanide‐induced shift (LIS) on the signals of the carbons and the splitting of some signals, which allowed the enantiomeric differentiation. As expected, the LIS decreased with the number of bonds between the binding function and the considered carbon. The enantiomeric splitting is observed for several signals in the spectrum of each compound. The influence of the hindrance of the binding function (primary, secondary or tertiary alcohol) and that of the stereochemistry of the double bonds is discussed. Copyright © 2004 John Wiley & Sons, Ltd.