Palladium-Catalyzed Nucleophilic Allylation of Aldehydes or Aldimines

Key words

allylation - vinylcyclopropanes - palladium

Significance

Ring-expansion reactions of vinylcyclopropanes are powerful tools for organic ­synthesis. The authors describe the palladium-catalyzed nucleophilic allylation of aldehyde and aldimines with vinylcyclopropane in the presence of dimethylzinc.

 

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Comment

The allylation of aldehydes with vinylcyclopropane and diethylzinc proceeded to provide homoallyl alcohols with anti stereoselectivity. Aldimines prepared from aldehyde and primary amines in situ underwent a similar allylation to give homoallylamines with syn stereoselectivity. The products can be converted by reaction with a tetranuclear zinc cluster into γ-vinyl-δ-valerolactons and γ-vinyl-δ-valerolactams. The transformation is useful for the efficient synthesis of bioactive molecules.

 

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