Stork enamine alkylation

The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or other electrophile to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. Since enamines are generally produced from ketones or aldehydes, this overall process (known as the Stork enamine synthesis) constitutes a selective monoalkylation of a ketone or aldehyde, a process that may be difficult to achieve directly.

The reaction is named after its inventor, Gilbert Stork (Columbia University).