Claisen condensations and

Michael reaction
McMurry, J. Organic Chemistry 7th Edition, Chapters 23:
The Claisen condensations: 23.7 – 23.9; The Michael reaction: 23.10.
The Claisen condensation reaction
• Condensation reaction between two ester molecules to yield a b-keto
ester.
• Mechanism is similar to that of the aldol reaction, but the tetrahedral
intermediate loses an alkoxide to give the product.
Mixed Claisen condensation
• Reactions successful if one of the esters does not have a-hydrogens.
The Dieckmann Condensation
• Intramolecular Claisen condensation, carried out with diesters.
• Useful for synthesis of five-membered and six-membered cyclic b-
keto esters from 1,6-diesters and 1,7-diesters respectively.
The Michael Reaction
• Addition of an enolate to a b-carbon of an a,b-unsaturated carbonyl
compound to give a conjugate addition product.
• Enolates that work best are those flanked by two EWGs (stable
enolates) such as enolates of b-diesters, b-keto esters and b-keto
nitriles.
• Unsaturated ketones, aldehydes, esters, amides and nitro compounds
can all act as electrophiles in the Michael reaction.
• The enolate is referred to as Michael donor while the electrophile is
called a Michael acceptor.
The Michael reaction
• General mechanism:
The Michael reaction
• Examples: