Fundamental Developments of Chiral Phase Chromatography in Connection with Enantioselective Synthesis of β-Amino Acids

Abstract

A few decades ago, the enantiomeric purities of chiral compounds were usually determined by comparison of experimental optical rotations or by preparation of diastereomeric derivatives followed by analysis of their ¹H NMR spectra. This situation changed when Emanuel Gil-Av, Binyamin Feibush and Rosita Charles-Sigler achieved the separation of single enantiomers from racemic α-amino acids by means of a chiral stationary phase. Indeed, chiral chromatography allowed a direct comparison of chromatograms obtained from enantiopure samples with those recorded with their racemates. With the aim of celebrating the relevance of Gil-Av's achievement, this review also presents several applications of chiral chromatography in the area of asymmetric synthesis of β-amino acids.