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

Renat Kadyrov,Jens Holz,Benjamin Schäffner,Odalys Zayas,Juan Almena,Armin Börner

doi:10.1016/j.tetasy.2008.04.019

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

Renat Kadyrov, Jens Holz + Show 4 more

https://doi.org/10.1016/j.tetasy.2008.04.019

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Journal: Tetrahedron: Asymmetry	Publication Date: May 1, 2008
Citations: 35

Affiliation: Evonik (Germany), Leibniz Institute for Catalysis, University of Rostock

#High Enantioselectivities #Excellent Yields + Show 8 more

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Abstract

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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