Abstract
AbstractAn optimized condition for the rhodium-catalyzed ring-opening reaction of C1-substituted oxabicyclic alkenes with aryl boronic acids was developed and the effect of aryl boronic acid as well as the effect of C1 substitution on the oxabicyclic alkenes was studied. Aryl boronic acids carrying electron-donating substituents provided the ring-opened products in excellent yields regardless of the position, while electron-withdrawing substituents were more susceptible to steric interactions. Although two different regioisomers are possible, all the rhodium-catalyzed ring-opening reactions of C1 substituted oxabicyclic alkenes studied with aryl boronic acids were found to be highly regioselective, giving single regioisomers in all cases.
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