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Synfacts 2007(12): 1288-1288  
DOI: 10.1055/s-2007-991353
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Direct Mannich Reactions: Synthesis of Protected anti-α,β-Diamino Acids

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
G. A. Cutting, N. E. Stainforth, M. P. John, G. Kociok-Köhn, M. C. Willis*
University of Bath, University of Oxford and GlaxoSmithKline, Stevenage, UK
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

This report describes a direct catalytic Mannich reaction which generates α,α-di­amino acids in one step. This is a very important structural motif in many medicinal agents and biologically active compounds. Magnesium perchlorate is the Lewis acid used and the DBFox ligand 1 provides the chiral induction. N-Tosyl imines were chosen as the one reacting partner while isothiocyanate-substituted oxazolidinones were the other nitrogen-containing reactant.