Enamide Derivatives: Versatile Building Blocks for Total Synthesis

Thibaut Courant; Guillaume Dagousset; Géraldine Masson

doi:10.1055/s-0034-1378706

Synthesis, Table of Contents

Synthesis 2015; 47(13): 1799-1856
DOI: 10.1055/s-0034-1378706

review

Enamide Derivatives: Versatile Building Blocks for Total Synthesis

Thibaut Courant

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Email: Geraldine.Masson@cnrs.fr

,

Guillaume Dagousset

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Email: Geraldine.Masson@cnrs.fr

,

Géraldine Masson*

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France Email: Geraldine.Masson@cnrs.fr

› Author Affiliations

Abstract

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Abstract

Enamides and enecarbamates are versatile building blocks in organic synthesis. This review describes the development of enamide chemistry and the utility of the resulting products in the synthesis of a variety of important, biologically active molecules.

1 Introduction

2 Asymmetric Hydrogenation of Enamides

3 Monofunctionalization of Enamide Derivatives

3.1 Palladium-Catalyzed α-Functionalization of Enamide Derivatives

3.2 Ruthenium-Catalyzed β-Functionalization of Enamide Derivatives

4 Ionic Vicinal Difunctionalization of Enamide Derivatives

4.1 Tandem Difunctionalization of Enamide Derivatives

4.2 Cycloadditions

4.2.1 [4+2] Cycloadditions

4.2.2 [2+2] Cycloadditions

4.2.3 Cyclopropanation of Enamides

4.3 Other Pericyclic Reactions

4.3.1 Electrocyclization Reactions

4.3.2 Overman Rearrangement

4.4 Platinum-Catalyzed Vicinal Difunctionalization of Enamide Derivatives

5 Radical Vicinal Difunctionalization of Enamide Derivatives

6 Oxidative Vicinal Difunctionalization of Enamide Derivatives

7 N-Arylation of Enecarbamates

8 Conclusion

9 Ligand Glossary

Key words

enamide - total synthesis - alkaloid - hydrogenation - functionalization

Full Text

References

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