Synthesis 2013; 45(20): 2769-2812
DOI: 10.1055/s-0033-1339479
review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Metal-Catalyzed Asymmetric Mannich Reactions

Babak Karimi*
a  Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195-1159, Gava Zang, Zanjan, Iran   Fax: +98(241)4214949   Email: karimi@iasbs.ac.ir
,
Dieter Enders
b  Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany
,
Ehsan Jafari
a  Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195-1159, Gava Zang, Zanjan, Iran   Fax: +98(241)4214949   Email: karimi@iasbs.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 25 April 2013

Accepted after revision: 12 June 2013

Publication Date:
17 September 2013 (online)


Abstract

In this review, recent works on metal-catalyzed asymmetric Mannich, aza-Henry and vinylogous Mannich reactions are described. The asymmetric Mannich reaction is one of the most powerful methodologies among the carbon–carbon bond-forming reactions, and provides direct access to a wide range of optically active natural products with useful biological properties.

1 Introduction

2 Catalytic Asymmetric Mannich Reactions

2.1 BINOL Ligands

2.2 BINAP Ligands

2.3 Bisoxazoline Ligands

2.4 Pyridine Bisoxazoline Ligands

2.5 Diamine Ligands

2.6 P,N-Ligands

2.7 P,S-Ligands

2.8 P,P-Ligands

2.9 N,N-Ligands

2.10 Miscellaneous

3 Asymmetric Aza-Henry Reactions

3.1 BINOL Ligands

3.2 Bisoxazoline Ligands

3.3 N,N-Ligands

3.4 Miscellaneous

4 Asymmetric Vinylogous Mannich Reactions

5 Conclusion

 
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