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Asymmetric Synthesis of Functionalized Tetrasubstituted α‑Aminophosphonates through Enantioselective Aza-Henry Reaction of Phosphorylated Ketimines

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journal contribution
posted on 02.01.2015, 00:00 by Javier Vicario, Pablo Ortiz, José M. Ezpeleta, Francisco Palacios
Bifunctional Cinchona alkaloid thioureas efficiently catalyze asymmetric nucleophilic addition of nitromethane to ketimines derived from α-aminophosphonic acids to afford tetrasubstituted α-amino-β-nitro-phosphonates. Catalytic hydrogenation of (S)-α-amino-β-nitro-phosphonate 2d gives enantiopure (S)-α,β-diaminophosphonate 3.

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