Nickel-Catalyzed Enantioselective Hydrogenation of β-(Acylamino)acrylates: Synthesis of Chiral β-Amino Acid Derivatives

The nickel-catalyzed asymmetric hydrogenation of beta-(acylamino)acrylates has been developed, affording chiral beta-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of beta-alkyl and beta-aryl beta-(acylamino)acrylates. The synthesis of chiral beta-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.