Abstract
This research is concerned with the studies of oxidation reactions of mask o-benzoquinones using Oxone or mCPBA as oxidants. The oxidation of MOBs could afford epoxidation products or novel rearrangement products via initial Baeyer-Villiger oxidation to form a highly functionalized 5,5-disubstituted 2(5H)-furanones depending on the substituents on MOBs and the reaction condition in the presence or absence of NaHCO3. Oxidation of MOBs in a neutral to acidic condition would give epoxidation of MOB at C4,C5-position, whereas the presence of NaHCO3 during oxidation lead to a Baeyer-Villiger oxidation at the carbonyl position followed by sequential ring cleavage and lactone formation to furnish 2(5H)-furanones. In this research we also have investigated the effect of installing chiral auxiliary on MOB to induce diastereoselectivity during the newly found tandem oxidation-rearrangement reaction of MOBs.