Stork-Enamine Reaction

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This reaction is like the Michael reaction, except an enamine, not an enolate ion, is used as the nucleophile to attack either an alpha, beta-unsaturated aldehyde or an alpha, beta-unsaturated ketone. The addition of this aldehyde or ketone is followed by a second step to hydrolyze the enamine back to a carbonyl group. The mechanism is as follows:

Stork.jpg