Chemistry Letters, Vol.33, No.6, 764-765, 2004
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 stereo specifically 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.