Synthesis of chiral β-aminophosphonates via Rh-catalyzed asymmetric hydrogenation of β-amido-vinylphosphonates

The Rh-catalyzed asymmetric hydrogenation of prochiral β-N-acetylamino-vinylphosphonates allows the preparation of chiral β-N-acetylamino-phosphonates with excellent yields (up to 100%) and high enantioselectivities (up to 92% ee). The reaction is strongly dependent on the chiral bidentate phosphorus ligand and the solvent employed. In several cases an inversion of the induced chirality was noted by using the corresponding E- or Z-isomeric substrates.

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