Enamide Derivatives: Versatile Building Blocks for Total Synthesis

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

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