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

Article type: Research Article

Authors: Merelli, Bérangère | Menguy, Laurence | Soubeyrand-Lenoir, Estelle | Cherton, Jean-Claude

Affiliations: Institut Lavoisier (UMR 8180), Université de Versailles Saint-Quentin en Yvelines, 45 Avenue des Etats-Unis 78035, Versailles Cedex, France

Note: [] Part of Thesis.

Note: [] Corresponding author. Tel.: +331 39 25 44 54; Fax: +331 39 25 44 52; E-mail: [email protected], [email protected].

Abstract: Studies of the perturbing effect of chiral solvating agents (CSAs) namely the fluoroalcohols 5a and 5b upon the NMR spectra of chiral Δ2-thiazolines 1 presenting interesting insecticidal properties demonstrated the ability of these CSAs to afford diastereomeric solvates from these substrates providing their enantiomeric discrimination. Thus, for five of the six tested Δ2-thiazolines 1A and 1B there is at least one possibility to proceed to their enantiomeric discrimination either by 1H or 19F NMR using mostly 5b as CSA.

Keywords: [TeX:] $\Delta^{2}$-thiazolines-1,3, stereomer, enantiomer, chiral solvating agent, optical purity analysis

Journal: Spectroscopy, vol. 20, no. 3, pp. 95-107, 2006