Configurational assignment of optically active hydroperoxy homoallylic alcohols and the corresponding diols by circular dichroism and multidimensional gas chromatography

Allylic hydroperoxides are a class of compounds of versatile synthetic utility. Optically active diastereomeric hydroperoxy homoallylic alcohols and their corresponding diols are easily available through horseradish peroxidase (HRP)-catalyzed kinetic resolution of racemic hydroperoxides. Here we describe the assignment of the absolute configuration of the optically active products and substrates obtained after HRP-catalysis by the circular dichroism exciton chirality method. Moreover, the analytical-scale separation of the enantiomers based on multidimensional gas chromatography on chiral columns is presented. Since the enantiomeric elution order on the ciral columns was constituted, the absolute stereochemistry of optically active allylic diols can easily be deduced by their retention times on β-cyclodextrins. Chirality 9:69–74, 1997.