Synthesis of three new cyclodextrin derivatives and their application as chiral stationary phases in the determination of optical purity by capillary gas chromatography

Three cyclodextrin (CD) derivatives were synthesized by substituting the 2,6-OH groups of cyclodextrin with benzyl and the 3-OH group with three different acyl groups (valeryl, heptanoyl, octanoyl). The chromatographic properties of the three CD derivatives were investigated. These derivatives can separate not only the chlorotoluene and xylene isomers but also some racemic compounds, such as methyl trans-2,2-dimethyl-3-(2-methylpropenyl)cyclopropane-carboxylate. Using these CD derivatives as chiral stationary phases, the optical purity of 1-(2,4-dichlorophenyl) ethanol obtained by asymmetric catalytic hydrogenation of 2,4-dichloroacetophone and trans-2,3-epoxyhexanol synthesized by Sharpless epoxidation of trans-2-hexen-1-ol was determined and the catalytic reaction was evaluated.