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

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.