126504-48-1Relevant articles and documents
Chiral Recognition of Diastereomeric Esters and Acetals by EPR and NMR Investigations
Maeurer, Manfred,Stegmann, Hartmut B.
, p. 1679 - 1685 (2007/10/02)
The reaction of the racemic phenols I and II with chiral auxiliaries like the acid chloride III and particularly the lactols IV and V (Noe's reagent) leads to diastereomeric esters and acetals, respectively.The products may be synthesized either in the EPR sample tube or under preparative conditions with subsequent separation of the diastereomers by chromatographic methods.Oxidation of the phenols with lead dioxide in inert solvents provides the corresponding phenoxyls, which are investigated by EPR and ENDOR spectroscopy.The most striking features of these spectra are the differences in the β-proton coupling constants of up to several Gauss, indicating a significant alteration of the hyperconjugation angle.These results are interpreted in terms of the population of specific conformations favored by stereoelectronic and steric interactions, which are confirmed by careful investigations of the shielding and deshielding effects in the 1H-NMR spectra of the corresponding phenols.