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- Stetter_reaction abstract "The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors. Unlike 1,3-dicarbonyls, which are easily accessed through the Claisen condensation, or 1,5-dicarbonyls, which are commonly made using a Michael reaction, 1,4-dicarbonyls are challenging substrates to synthesize, yet are valuable starting materials for several organic transformations, including the Paal-Knorr synthesis of furans and pyrroles. Traditionally utilized catalysts for the Stetter reaction are thiazolium salts and cyanide anion, but more recent work toward the asymmetric Stetter reaction has found triazolium salts to be effective. The Stetter reaction is an example of umpolung chemistry, as the inherent polarity of the aldehyde is reversed by the addition of the catalyst to the aldehyde, rendering the carbon center nucleophilic rather than electrophilic.".
- Stetter_reaction thumbnail Stetter_reaction_general_example.png?width=300.
- Stetter_reaction wikiPageID "4436559".
- Stetter_reaction wikiPageRevisionID "589165880".
- Stetter_reaction hasPhotoCollection Stetter_reaction.
- Stetter_reaction subject Category:Addition_reactions.
- Stetter_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Stetter_reaction subject Category:Name_reactions.
- Stetter_reaction type AdditionReaction113427356.
- Stetter_reaction type AdditionReactions.
- Stetter_reaction type ChemicalProcess113446390.
- Stetter_reaction type ChemicalReaction113447361.
- Stetter_reaction type NameReactions.
- Stetter_reaction type NaturalProcess113518963.
- Stetter_reaction type PhysicalEntity100001930.
- Stetter_reaction type Process100029677.
- Stetter_reaction comment "The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors.".
- Stetter_reaction label "Stetter reaction".
- Stetter_reaction label "Stetter-Reaktion".
- Stetter_reaction label "Stetter反应".
- Stetter_reaction sameAs Stetter-Reaktion.
- Stetter_reaction sameAs m.0c298w.
- Stetter_reaction sameAs Q904710.
- Stetter_reaction sameAs Q904710.
- Stetter_reaction sameAs Stetter_reaction.
- Stetter_reaction wasDerivedFrom Stetter_reaction?oldid=589165880.
- Stetter_reaction depiction Stetter_reaction_general_example.png.
- Stetter_reaction isPrimaryTopicOf Stetter_reaction.