O-Methylatrolactic acid as a new reagent for determination of the enantiomeric purity and absolute configuration of chiral alcohols and amines

Abstract

Easily available in both enantiomeric forms, O-methylatrolactic acid (MAA) was successfully used as a new chiral derivatizing agent. Enantiomeric purities and the absolute configurations of chiral secondary alcohols and amines were determined using the observed differences in 1H NMR chemical shifts. The Mosher’s stereochemical model explains the conformational preferences of the respective diastereomeric MAA esters and amides. This was confirmed by the results of DFT calculations for the respective conformers.