One-pot dialkylation of allylphenylsulfide induced by aminoalkoxides- activated NaNH2. Application to the synthesis of unsymmetrical ketones

Article abstract of DOI:10.1016/S0040-4020(99)00481-0

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.