Synthesis of Optically Active Substituted Cyclohexenones from Carbohydrates by Catalytic Ferrier Rearrangement

Article abstract of DOI:10.1246/bcsj.64.2118

Conversion of hex-5-enopyranosides into substituted cyclohexenones (Ferrier rearrangement) was found to proceed efficiently with a catalytic amount of various mercury(II) salts at room temperature in a neutral solvent system.Among the mercury(II) salts tested, mercury(II) trifluoroacetate showed the highest activity.Four optically active cyclohexenones were prepared from hex-5-enopyranosides utilizing this method.