Stork Enamine Alkylation: α‑Alkylation Without Strong Base (Enamine Strategy)

Learn Stork enamine alkylation: form an enamine, do SN2 alkylation, then hydrolyze back to the carbonyl. Why it avoids over-alkylation.

• Reaction: Carbonyl → α-alkylated carbonyl (via enamine)
• What it does: Uses enamines as 'soft' enolate equivalents
• Typical reagents: 1) Secondary amine (pyrrolidine) 2) R–X 3) Hydrolysis
• Key intermediate: Enamine
• Driving force: Enamine C is nucleophilic; hydrolysis regenerates carbonyl
• Exam type: Synthesis planning
• Exam type: Regioselectivity