Asymmetric hydrogenation of methyl α-benzamido cinnamate in ionic liquid solvent

The room temperature ionic liquid EMIMOTf was employed as the sole reaction solvent for the asymmetric hydrogenation of methyl α-benzamido cinnamate. Under conditions of 60 psi hydrogen and 50 °C for 24 h, near quantitative conversions were observed using both the achiral DiPFc–Rh catalyst, and the chiral EtDuPHOS–Rh catalysts. Enantiomeric excess of 89% ee was observed for hydrogenations carried out with the chiral catalyst.