Recent Advances in the N-Heterocyclic Carbene (NHC)-Organocatalyzed Stetter Reaction and Related Chemistry

Abstract

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

Key words

N-heterocyclic carbenes - Stetter reaction - organocatalysis - umpolung - asymmetric catalysis

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