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Synfacts 2006(10): 1028-1028  
DOI: 10.1055/s-2006-949286
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Three-Component Synthesis ofα,β-Diamino Acid Derivatives

Contributor(s): Mark Lautens, Frédéric Ménard
M. M. Salter, J. Kobayashi, Y. Shimizu, S. Kobayashi*
The University of Tokyo, Japan
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

The method is the first pure direct three-component Mannich reaction and it is also the first using glycine ester as nucleophile. Indeed, N-diarylmethyleneglycinates (3 and 5) were shown to be activated by the Zn(OTf)2 Lewis acid and to act as potent nucleophiles in trapping of the iminium ions formed in situ. In earlier methods, only formaldehyde was used as a non-enolizable aldehyde precursor to the iminium ion, or the amine component was limited to aniline derivatives.