Determination of the enantiomeric composition of chiral delta-2-oxazolines-1,3 by 1H and 19F NMR spectroscopy using chiral solvating agents

Abstract : Studies of the perturbing effect of chiral solvating agents (CSAs) 5a and mostly of 5c upon the NMR spectra of chiral Delta(2)-oxazoline 1 demonstrated the ability of these fluoroalcohols to afford diastereomeric solvates from these solutes. Thus, for all tested Delta(2)-oxazolines 1Aa-d, 1Ba, and 1e there is at least one possibility to proceed to their enantiomeric discrimination either by (1)H or (19)F NMR using these CSAs (see Fig. 1). NMR results are discussed from substrate and CSA structure standpoints and a solvation model is proposed on the basis of the inequivalence senses generally observed. Then the method was applied to extracts of incubated locust tissues obtained by solid phase extraction (SPE) after a partial unmasking of the substrate 1.
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M. Beaufour, B. Merelli, L. Menguy, J.-C. Cherton. Determination of the enantiomeric composition of chiral delta-2-oxazolines-1,3 by 1H and 19F NMR spectroscopy using chiral solvating agents. Chirality, Wiley, 2003, 15 (5), pp.382-390. ⟨10.1002/chir.10225⟩. ⟨hal-02087633⟩

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