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

Feng Zhou; Fu-Min Liao; Jin-Sheng Yu; Jian Zhou

doi:10.1055/s-0034-1379255

Synthesis, Table of Contents

Synthesis 2014; 46(22): 2983-3003
DOI: 10.1055/s-0034-1379255

review

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

Feng Zhou

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N Zhongshan Road, Shanghai 200062, P. R. of China Fax: +86(21)62234560 Email: jzhou@chem.ecnu.edu.cn

,

Fu-Min Liao

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N Zhongshan Road, Shanghai 200062, P. R. of China Fax: +86(21)62234560 Email: jzhou@chem.ecnu.edu.cn

,

Jin-Sheng Yu

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N Zhongshan Road, Shanghai 200062, P. R. of China Fax: +86(21)62234560 Email: jzhou@chem.ecnu.edu.cn

,

Jian Zhou*

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N Zhongshan Road, Shanghai 200062, P. R. of China Fax: +86(21)62234560 Email: jzhou@chem.ecnu.edu.cn

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Abstract

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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

Full Text

References

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