It is shown that the activation of NaNH2 by sodium aminoalkoxides, leading to new superbases, induced an efficient one-pot dialkylation of allylphenylsulfide. The regioselectivity of the reaction (α, α′ vs α, γ) was found as strongly dependent on the nature of the alkyl halide. As an application, α, γ dialkylated products were efficiently converted into the corresponding unsymmetrical ketones.
