Recent Advances in the Carbon–Carbon Bond-Forming Reactions of N-Acylketimines

Dedicated to Professor Herbert Mayr on the occasion of his 70^th birthday

Abstract

N-Acylketimines are important synthetic building blocks used in the synthesis of a wide variety of functional amino compounds including cyclic and acyclic products. This review focuses on carbon–carbon bond-forming reactions of N-acylketimines to construct amino compounds having tetrasubstituted carbon centers.

1 Introduction

2 Preparation of N-Acylketimines

2.1 Nucleophilic Addition of Amide Derivatives

2.2 Acylation of Imine Derivatives

2.3 An Aza-Wittig-Type Reaction

2.4 Oxidation of Amine Precursors

3 Reactions of N-Acylketimines

3.1 Cyclic Ketimines

3.2 Acyclic Ketimines

4 Conclusions

Key words

N-acylketimine - C–C bond-forming - nucleophilic addition - electrophilicity - asymmetric synthesis

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