1H and2H nuclear magnetic resonance determination of the enantiomeric purity and absolute configuration of α-deuteriated primary carboxylic acids, alcohols, and amines

Abstract

The enantiomeric composition and absolute configuration of α-deuteriated primary carboxylic acids may be accurately determined by 1H and 2H nuclear magnetic resonance analysis of the corresponding esters of (S)-methyl 2-hydroxy-2-phenylethanoate (2). Similar methods with (S)-2-acetoxy-2-phenylethanoic acid (3) and (–)-camphanoyl chloride (1) as chiral reagents have enabled the enantiomeric purity of α-deuteriated primary alcohols and primary amines to be assayed. These chiral reagents may also be used to determine the enantiomeric composition of chiral secondary acids, alcohols, and amines.