Catalytic Asymmetric Electrophilic Amination Reactions To Form Nitrogen-Bearing Tetrasubstituted Carbon Stereocenters

Abstract

The catalytic asymmetric electrophilic amination has been established as a fruitful methodology for the construction of nitrogen-bearing tetrasubstituted carbon stereocenters, with its roots nourished by the latest achievements in chiral catalysis and synthetic strategies. This review summarizes the recent progresses, briefly discusses the reaction mechanism and challenges in this context, and outlines synthetic opportunities for future development.

1 Introduction

2 Transformations Based on Azodicarboxylates

2.1 α-Substituted Prochiral Aldehydes and Ketones

2.2 Ketenes

2.3 Doubly Activated Dicarbonyl Compounds

2.4 Heteroatom-Containing Activated Methines

2.5 Heterocyclic Nucleophiles

3 Amination Reactions Using other Amination Reagents

4 Conclusion

Key words

amination - asymmetric catalysis - tetrasubstituted carbon - stereogenic center - Lewis acid catalysis - organocatalysis

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