An Original On-Column Oxidative Cleavage of Vicinal Diols Using Alumina/Potassium Periodate: Application to Sequential Oxidation/Horner-Emmons Reactions

An unprecedented simple on-column solvent-free oxidative cleavage of vicinal diols in the solid phase using alumina/potassium metaperiodate is described herein. It permits preparation of the corresponding carbonyl compounds with high purity and good to excellent yields requiring only short reaction times. This methodology is then employed in on-column sequential oxidation/Horner-Emmons reactions for the preparation of selected stilbenes in good yields where both reaction and purification are integrated in a single unit or occur simultaneously permitting the rapid and easy preparation of small samples of pure stilbenes.