Stork Enamine Reaction Mechanism - Alkylation, Acylation, & Michael Addition

TL;DR

The Stork and Amine reaction involves the formation of an enamine intermediate, which can be used for alkylation, reaction with acid chloride, and participation in a Michael reaction. The mechanism involves protonation, nucleophilic attack, and transfer of hydrogen atoms.

Transcript

in this video we're going to briefly review the stork and amine reaction so let's say we have this particular molecule cyclohexanol and we're going to react it with a secondary amine whenever you react to ketone with a secondary amine you're going to get an enamine and so our product will look like this we're going to have a single bond between the... Read More

Key Insights

• 💁 The Stork and Amine reaction involves the formation of an enamine intermediate, which can be used for various reactions.
• ❓ Alkylation, reaction with acid chloride, and participation in a Michael reaction are some of the reactions that can be carried out using the enamine intermediate.
• 👊 The mechanism of the Stork and Amine reaction involves protonation, nucleophilic attack, and transfer of hydrogen atoms.
• 😥 The pH of the reaction system plays a crucial role in the formation of the enamine intermediate.
• 👊 The enamine intermediate acts as a nucleophile and attacks electrophilic carbon atoms.
• 💦 The enamine intermediate can be generated using a weak base such as water or another secondary amine.
• ❓ The enamine intermediate undergoes hydrolysis to regenerate the original ketone product.

Summary & Key Takeaways

• The Stork and Amine reaction starts with the reaction between a ketone and a secondary amine to form an enamine intermediate.

• The enamine intermediate can be alkylated using an alkyl halide, resulting in the formation of an iminium ion.

• The iminium ion can be hydrolyzed with H3O+ to regenerate the original ketone.

• The enamine intermediate can also react with an acid chloride to form an iminium ion, which can be further hydrolyzed to give a ketone product.

• Additionally, the enamine intermediate can participate in a Michael reaction with an alpha beta unsaturated aldehyde or ketone, resulting in the formation of a 1,5-dicarbonyl product.