Enamine Reactions for Carbonyl Functionalization

Enamine reactions can be used to make alpha-substituted ketones and aldehydes. This chemistry is known as the Stork enamine reaction, named after Gilbert Stork. It gives students a clear example of how a carbonyl compound can be modified at the alpha carbon, which is the carbon next to the carbonyl group.

The Stork enamine reaction generates α-substituted carbonyls via enamine intermediates.

In enamines, the conjugation between nitrogen's lone pair and the C=C bond leads to its resemblance to enolate ions, with both accommodating a nucleophilic α carbon atom.

Despite this, enamines are neutral and less reactive than enolates that ca...