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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.

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 ed. in English) (2012-11-07)
Matthew J Hesse, Craig P Butts, Christine L Willis, Varinder K Aggarwal
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.

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Hydrofluoric acid, 48 wt. % in H2O, ≥99.99% trace metals basis
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Potassium hydrogenfluoride, 99%
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Hydrofluoric acid, ACS reagent, 48%
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