Prediction of the Absolute Configurations of the Enantiomers of Racemic Primary and Secondary Alcohols and Primary Amines by Kinetic Resolution with (2R,3R)-2,3-Diacetoxysuccinic Anhydride

Abstract

The absolute configurations of the enantiomers of a variety of racemic secondary and primary alcohols and racemic primary amines have been correctly predicted from the results of kinetic resolution with (2R,3R)-2,3-diacetoxysuccinic anhydride. In the prediction model (1), allocation of relative sizes to the groups attached to the chiral centre was based on conformational free energy differences.