Matthew J. Hesse, Dr. Craig P. Butts, Prof. Christine L. Willis and Prof. Varinder K. Aggarwal Diastereodivergent Synthesis of Trisubstituted Alkenes through Protodeboronation of Allylic Boronic Esters: Application to the Synthesis of the Californian Red Scale Beetle Pheromone Angewandte Chemie International Edition 51
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.
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