Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: Application to the synthesis of the californian red scale beetle pheromone
E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF·3 H2O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF2/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle. Copyright
Hesse, Matthew J.,Butts, Craig P.,Willis, Christine L.,Aggarwal, Varinder K.