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Direct Mannich Reactions: Synthesis of Protected anti-α,β-Diamino Acids
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
22 November 2007 (online)
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.