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

The Rh-catalyzed asymmetric hydrogenation of prochiral beta-N-acetylamino-vinylphosphoniites allows the preparation of chiral beta-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. (C) 2008 Elsevier Ltd. All rights reserved.