Open AccessDetermination of the enantiomeric composition of chiral delta-2-thiazolines-1,3 by1H and19F NMR spectroscopy using chiral solvating agents
Author(s) -
B. Merelli,
Laurence Menguy,
Estelle SoubeyrandLenoir,
JeanClaude Cherton
Publication year - 2006
Publication title -
journal of spectroscopy
Language(s) - English
Resource type - Journals
eISSN - 2314-4920
pISSN - 2314-4939
DOI - 10.1155/2006/698685
Subject(s) - diastereomer , enantiomer , chemistry , nuclear magnetic resonance spectroscopy , nmr spectra database , chirality (physics) , stereochemistry , enantiomeric excess , chiral derivatizing agent , spectroscopy , composition (language) , proton nmr , spectral line , organic chemistry , enantioselective synthesis , chiral symmetry , chiral column chromatography , catalysis , physics , particle physics , quantum mechanics , nambu–jona lasinio model , linguistics , philosophy , quark , astronomy
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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