Highly efficient resolution of racemic diethanolamine using (-) camphor-10-sulphonic acid

Abstract

Ring opening of two equivalents of racemic styrene epoxide by benzylamine gives rise to racemic mixture of 2-(benzyl -(2-hydroxy-2-phenylethyl)-amino)-1- phenylethanol, among other diethanolamine products. The racemic mixture is efficiently separated into its enantiomers by complexation with (-) camphor-10-sulphonic acid. The corresponding diastereomeric complex was also characterized by single crystal X-ray diffraction method. This resolution method offers an economically more viable route for the isolation and use of the chiral ligand that has proved to be useful in many asymmetric catalysis reactions. © ARKAT.