Stereochemical effects in mass spectrometry XIII—Determination of absolute configuration by fast atom bombardment mass spectrometry

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Abstract
It was found that in the fast atom bombardment mass spectra of some asymmetric secondary alcohols and amines, when a pair of enantiomers, such as (2R,3R)‐ and (2S,2S)‐2,3‐diacetoxysuccinic anhydride and (2R,3R)‐ and (2S,3S)‐2,3‐dibenzoyloxysuccinic anhydride, were used as reagents, the relative abundances of characteristic ions formed by the stereoselective reaction between a sample and a reagent of different configurations were much higher than those of ions formed by a sample and a reagent of the same configuration. The absolute configurations of the sample molecule may be predicted by examination of the mass spectra of the sample measured with reagents of R and S configurations. This approach proved to be a convenient way to determine the absolute configuration of organic molecules at the micromole level by fast atom bombardment mass Spectrometry, and it has advantages over the chemical ionization method reported previously for the analysis of polar and involatile compounds.