Stork Enamine Synthesis

Klein 21.11. Enamine formation is already taught with aldehydes and ketones. This page uses the enamine to alkylate.

• A secondary amine, often pyrrolidine, converts a ketone to an enamine.
• The enamine carbon reacts with a reactive alkyl halide or an α,β-unsaturated carbonyl in a Michael addition.
• Hydrolysis returns the carbonyl and releases the amine.
• Why this is a milder alternative to forming an enolate with LDA.
• One alkylation example and one Michael example.