Some of the advantages of using an enamine over and enolate are enamines are neutral, easier to prepare, and usually prevent the overreaction problems plagued by enolates. These reactions are generally known as the Stork enamine reaction after Gilbert Stork of Columbia University who originated the work.

What are enamines used for?

Enamines are used as intermediates to form carbon–carbon bonds in reactions that parallel those of carbonyl compounds. The carbon–carbon double bond is nucleophilic because the lone pair electrons of nitrogen can be released to the carbon atom that was the α carbon atom of the original carbonyl compound.

Are enamines stable?

Enamines can be efficiently cross-coupled with enol silanes through treatment with Ce(IV) ammonium nitrate. These reactions were reported by the Narasaka group in 1935, providing a route to stable enamines as well as one instance of a 1,4 diketone (derived from a morpholine amine reagent).