Ph3P catalyzed efficient synthesis of ethyl 2-(acetylanilino)-acrylates and ethyl (E)-3-(acetylanilino)-2-propenoates by nucleophilic addition to ethyl propiolate

The addition of acetanilides to ethyl propiolate proceeds under neutral conditions in the presence of triphenylphosphine to give the corresponding α-substituted alkyl acrylates together with variable amounts of the β-substituted isomer with (E) geometry. Addition of arylsulfonylanilides to alkyl propiolates under similar conditions, produced only the alkyl (E)-3-arylsulfonylanilino-2-propenoates.

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