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Recent Advances in the N-Heterocyclic Carbene (NHC)-Organocatalyzed Stetter Reaction and Related Chemistry
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2015
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EngineeringOrganic ChemistryChemistryHeterocycle ChemistryStetter Reaction 3Chemical EngineeringNovel OrganocatalystsStetter ReactionOrganometallic CatalysisRecent AdvancesCross-coupling ReactionDerivativesRelated ChemistryDiversity-oriented SynthesisCatalysisTotal Synthesis 7Asymmetric CatalysisBiomolecular EngineeringHeterocyclicAlkene MetathesisNatural Sciences
Recent developments in the N-heterocyclic carbene (NHC)-catalyzed umpolung of aldehydes followed by their interception with activated carbon–carbon double bonds, namely the Stetter reaction, are presented. Advances in the inter- and intramolecular versions of this reaction, enantioselective transformations as well as the use of unactivated olefins in this type of reaction are discussed. 1 Introduction 2 Proposed Mechanism of the Stetter Reaction 3 Intramolecular Stetter Reactions 4 Intermolecular Stetter Reactions 5 Hydroacylation Reactions 6 Applications in Total Synthesis 7 Conclusion