Highly regioselective α-alkylation of γ-acetoxy-α, β-enoates by reduction–alkylation with lithium dibutylcuprate–alkyl halides: application to the synthesis of spirovetivanes

Abstract

Reaction of γ-acetoxy-α, β-enoates with lithium dibutylcuprate followed by alkyl halides results in the predominant or exclusive formation of α-alkyl-β, γ-enoates in high yields under mild conditions; a synthetic route to (±)-α-vetispirene is also presented.