Stork enamine alkylation

[1] 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.

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

By using an anionic version of an enamine, known as an azaenolate or metalloenamine, it is also possible to alkylate ketones or aldehydes with alkyl halides as less reactive electrophiles:[4] In this method a carbonyl compound is condensed to a Schiff base.

The imine then reacts with a Grignard reagent to the corresponding Hauser base.

In the Corey-Enders reaction, a hydrazone replaces the amine for enantioselection.