(E)-(3-Chloro-1-methyl-1-propenyl)-
trimethylsilane acts as the alkylative
equivalent of 3-buten-2-one (methyl vinyl ketone), permitting
regiospecific enolate alkylation under nonequilibrating conditions.
As a vinylsilane it can be converted,via the corresponding
α,β-epoxy silane, into a 3-oxobutyl moiety, and hence used
in an alkylative equivalent of Robinson annulation.Application
of such methodology can be seen (eq 1) in the preparation of
bicyclodecenones via the alkylation of dihydrocarvone with this
reagent.Apart from this application, and its use in combination
with potassium iodide, it has seen little use so far.
