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Synthesis 2010(21): 3583-3595  
DOI: 10.1055/s-0030-1258241
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Recent Applications of α-Amido Sulfones as in situ Equivalents of Activated Imines for Asymmetric Catalytic Nucleophilic Addition Reactions

Biaolin Yin*a, Yuanxiu Zhanga, Li-Wen Xu*b
a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China
Fax: +86(20)87113735; e-Mail: blyin@scut.edu.cn ;
b Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, P. R. of China
Fax: +86(571)28865135; e-Mail: liwenxu@hznu.edu.cn;
Further Information

Publication History

Received 17 June 2010
Publication Date:
03 September 2010 (online)

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Abstract

Catalytic nucleophilic addition to the carbon-nitrogen double bond of an imino group in an asymmetric fashion provides a direct connective and attractive route to enantioenriched N-protected amines with structural diversity. In the last decades, significant achievements have been made in the field of catalytic enantioselective reactions involving the use of α-amido sulfones as in situ equivalents of activated imines. These, in combination with diverse nucleophiles, are used to prepare optically pure amines or N-protected amides. This review focuses on the recent advances in the synthetic applications of α-amido sulfones as reactive precursors of imines in the asymmetric addition of organometallic reagents, Mannich­, aza-Henry, Strecker, and other asymmetric nucleophilic addition reactions.

1 Introduction

2 Asymmetric Mannich-Type Reactions

2.1 Phase-Transfer-Catalyzed Mannich Reactions

2.2 Bifunctional Organocatalyzed Mannich Reactions

3 Catalytic Enantioselective Addition of Organometallic Reagents­

4 Catalytic Enantioselective Aza-Henry Reactions

5 Asymmetric Strecker Reactions

6 Miscellaneous Reactions

7 Summary and Outlook

Key words

nucleophilic addition - α-amido sulfone - N-acylimino derivatives - asymmetric catalysis - enantioselective