Palladium-catalyzed Stereospecific Epoxide-opening Reaction of (gamma),(delta)-Epoxy-(alpha),(beta)-unsaturated Esters with Boric Acid Leading to (gamma),(delta)-Diol Derivatives with Double Inversion of Configuration

A new palladium-catalyzed epoxide-opening reaction of (gamma),(delta)-epoxy-(alpha),(beta)-unsaturated esters with boric acid has been developed, which proceeds stereospecifically giving rise to the corresponding (gamma),(delta)-diol derivatives with double inversion of the configuration, i.e., with retention of configuration, in excellent yields. The new method provides a useful tool in organic synthesis including natural product synthesis.