Health Dictionary
Reliable, easy-to-read patient information on common medical conditions — written in plain language, free of jargon, and grounded in current evidence. Browse the most frequent diagnoses, understand what they mean for everyday life, and learn which steps and questions help you have a focused conversation with your doctor.
Stork enamine alkylation
Introduction
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.
The process:
- formation of an enamine from a ketone
- addition of the enamine to and alpha, beta-unsaturated aldehyde or ketone
- 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.
References
- ↑ McMurry, John (2003-03-21). Organic Chemistry (Hardcover)
|format=requires|url=(help) (6th edition ed.). Belmont, CA: Thomson-Brooks/Cole. ISBN 0-534-38999-6. - ↑ A New Method for the Alkylation of Ketones and Aldehydes: the C-Alkylation of the Magnesium Salts of N-Substituted Imines Gilbert Stork and Susan R. Dowd J. Am. Chem. Soc.; 1963; 85(14) pp 2178 – 2180; doi:10.1021/ja00897a040