Monomerization and Cyclization of Terpene-based Molecules for use in Separation of Right- and Left-Handed Enantiomers by Gas Chromatography

Abstract

In this study, the terpene-based compounds α-pinene and β-pinene were manipulated to contain both epoxide and alcohol functional groups such that they could cyclize into barrel-shaped oligomers. The purpose was to see whether or not a more useful alternative to cyclodextrins could be synthesized for use in separation of right-handed from left-handed enantiomers by gas chromatography with a chiral stationary phase. Extensive synthetic procedures were devised to create the monomers, and attempts were made to cyclize them by varying the solvent used in the cyclization reaction, the metal used for its nucleophilic ability and the “template effect,” and method of heating. High-resolution mass spectrometry was used to analyze potential oligomers after cyclization, and encouraging results were obtained.