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DOI: 10.1055/s-0030-1258241
Recent Applications of α-Amido Sulfones as in situ Equivalents of Activated Imines for Asymmetric Catalytic Nucleophilic Addition Reactions
Publikationsverlauf
Publikationsdatum:
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
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