Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: application to the synthesis of the Californian red scale beetle pheromone.

Matthew J Hesse, Craig P Butts, Christine L Willis, Varinder K Aggarwal

Index: Angew. Chem. Int. Ed. Engl. 51(50) , 12444-8, (2012)

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Abstract

E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF⋅3 H(2)O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF(2)/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 © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.