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Diastereodivergent Synthesis of Trisubstituted Alkenes through Protodeboronation of Allylic Boronic Esters: Application to the Synthesis of the Californian Red Scale Beetle Pheromone

Authors


  • We thank EPSRC, GSK, and the Bristol Chemical Synthesis DTC for funding, Frontier Scientific for their generous donation of boronic acids and esters, and Prof. Guy Lloyd-Jones and Alistair Lennox for useful discussions.

Abstract

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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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