Stork enamine alkylation

Stork enamine alkylation, also known as the Stork-Enamine reaction, involves the addition of an enamine to an alpha,beta-unsaturated carbonyl acceptor in a process similar to the Michael reaction ^[1]. The product is then hydrolyzed by an aqueous acid to produce a 1,5-dicarbonyl compound.

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The process:

1. formation of an enamine from a ketone
2. addition of the enamine to and alpha, beta-unsaturated aldehyde or ketone
3. hydrolysis of the enamine back to a ketone

The reaction is named after its inventor: Gilbert Stork.

In a special case of this reaction type it is also possible to alkylate ketones or aldehydes with alkyl halides as less reactive electrophiles ^[2]:

In this method a carbonyl compound is converted to an imine by alkylimino-de-oxo-bisubstitution with a primary amine. The imine is then reacted with an Grignard reagent to the corresponding magnesium salt to an intermediate capable of displacing a halide. Hydrolysis once again yields the alkylated ketone.

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