Synthesis 2014; 46(22): 2983-3003
DOI: 10.1055/s-0034-1379255
review
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 20 June 2014

Accepted after revision: 15 July 2014

Publication Date:
29 October 2014 (eFirst)

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

 
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