Lewis acid mediated domino allylation of diallylsilane to α,β-unsaturated ketones

Abstract

On treatment of diallyldiisopropylsilane and α,β-unsaturated ketones with BF₃·OEt₂, 1,4-addition of an allyl moiety and subsequent intramolecular allylation onto the β-silyl carbocation intermediate furnished domino allylation products. Oxidative cleavage of the carbon–silicon bond furnished bis-homoallylic alcohols in good yields.