Intramolecular Reactions of Hydroperoxides and Oxetanes:Stereoselective Synthesis of 1,2-Dioxolanes and 1,2-Dioxanes

摘要

The 5-exo openings of oxetanes by hydroperoxides proceed rapidly and stereospecificaiiy to furnish 1,2-dioxolanes.The corresponding 6-exo cyciizations are slower and proceed with moderate stereoseiectivity.In the case of hydroperoxy acetals,5-exo nucleophiiic transfer of aikoxide competes effectively with 6-exo attack by the hydroperoxide.