Asymmetric synthesis of beta-phosphono malonates via Fe2O3-mediated phospha-Michael addition to Knoevenagel acceptors.
[reaction: see text]. The first asymmetric P-C bond formation under heterogeneous conditions was achieved via a Fe2O3-mediated conjugate addition of a chiral phosphite to alkylidene malonates. The easy cleavage of the chiral auxiliary from the addition products leads to optically active beta-substituted beta-phosphono malonates in good yields and high enantiomeric excesses.
Tedeschi
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L
Institut für Organische Chemie, Rheinisch Westfälische Technische Hochschule, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany.
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D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D005290:Ferric Compounds / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010710:Phosphates / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D005290:Ferric Compounds; D007202:Indicators and Reagents; D008314:Malonates; D010710:Phosphates; C000499:ferric oxide