Claisen Condensation: Mechanism and Applications

This lecture covers the Claisen condensation reaction, a base-promoted condensation between esters leading to 1,3-dicarbonyl compounds. It explains the self-condensation and cross-Claisen condensation, highlighting the importance of enol form existence for successful reactions. The Dieckmann condensation and Thorpe-Ziegler condensation are also discussed, along with the preparation of activated esters. Enamine chemistry, including reactivity, equilibrium with imine, and enamine-based catalytic transformations, is presented. The lecture concludes with enantioselective reactions using L-Proline as a catalyst, such as the Aldol and Mannich reactions.

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Aldol condensation

An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to give a conjugated enone. The overall reaction equation is as follows (where the Rs can be H) Aldol condensations are important in organic synthesis and biochemistry as ways to form carbon–carbon bonds.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.

Ester

In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (). Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC.

Mannich reaction

In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl () functional group by formaldehyde () and a primary or secondary amine () or ammonia (). The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich.

Enol

In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene (olefin) with a hydroxyl group attached to one end of the alkene double bond (). The terms enol and alkenol are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves deprotonation at the α position to the carbonyl group—i.

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