Abstract
A palladium-catalyzed nucleophilic allylation of aldehydes with vinylcyclopropane in the presence of diethylzinc proceeded to provide homoallyl alcohols with anti stereoselectivity. Aldimines prepared from aldehyde and primary amines in situ underwent a similar nucleophilic allylation to give homoallylamines with syn stereoselectivity. The resulting homoallyl alcohols and homoallylamines could be converted by treatment with a tetranuclear zinc cluster into γ-vinyl-δ-valerolactones and γ-vinyl-δ-valerolactams, respectively.
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