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Synfacts 2013; 9(1): 0077
DOI: 10.1055/s-0032-1317771
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Mannich Reaction of Glycine Imines

Contributor(s):
Hisashi Yamamoto
,
Patrick Brady
Hernando E, Arrayás RG, * Carretero JC. * Universidad Autonóma de Madrid, Spain
Catalytic Asymmetric Mannich Reaction of Glycine Schiff Bases with α-Amido Sulfones as Precursors of Aliphatic Imines.

Chem. Commun. 2012;
48: 9622-9624
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

glycine imines - Mannich reaction - copper - Schiff bases

Significance

α,β-Diamino acids are valuable due to their presence in peptide-based drugs and ­other bioactive compounds. In this report, the ­authors have extended their copper-catalyzed Mannich reaction of glycine Schiff bases to imines derived from aliphatic aldehydes, which previously performed poorly.


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Comment

α-Amido sulfones are employed as imine precursors, due to the instability of imines derived from aliphatic aldehydes. Excellent enantio­selectivity and syn-selectivity is obtained for a variety of imines. The products have high synthetic applicability due to the orthogonal protection of the amines.


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