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A (cis)α,β-epoxy-γ,δ-vinyl-silane undergoes lithiation α to the silicon atom with retention of the configuration of the oxirane. This leads to new silylated vinyloxiranes with a quaternary silylated stereogenic carbon atom. We show here the possible and efficient rearrangement of a methyl substituted adduct into a β,γ-unsaturated-α-silylated ketone.
A new palladium-catalysed allylic alkylation affording silylated 3-vinyl-pyrrolidones has been developed. The method relies upon the interaction between a stabilised acetamide enolate anion and a silicon-containing nitrogen-tethered η 3 -allyl-palladium moiety. Two variants have been studied, involving location of the silicon atom on either olefinic carbon atom of the cyclisation precursor...
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