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Enantiomeric differentiation of acyclic terpenes by 13C NMR spectroscopy using a chiral lanthanide shift reagent

✍ Scribed by Marie-Cécile Blanc; Pascale Bradesi; Joseph Casanova

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
93 KB
Volume
43
Category
Article
ISSN
0749-1581

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✦ Synopsis

The 13C 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.

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