Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones

Bernier, Chad M.Merola, Joseph S.2021-05-252021-05-252021-05-24Bernier, C.M.; Merola, J.S. Design of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl Ketones. Catalysts 2021, 11, 671.http://hdl.handle.net/10919/103484A series of chiral complexes of the form Ir(NHC)2(aa)(H)(X) (NHC = N-heterocyclic carbene, aa = chelated amino acid, X = halide) was synthesized by oxidative addition of -amino acids to iridium(I) bis-NHC compounds and screened for asymmetric transfer hydrogenation of ketones. Following optimization of the reaction conditions, NHC, and amino acid ligands, high enantioselectivity was achieved when employing the Ir(IMe)2(l-Pro)(H)(I) catalyst (IMe = 1,3-dimethylimidazol-2-ylidene), which asymmetrically reduces a range of acetophenone derivatives in up to 95% enantiomeric excess.application/pdfenCreative Commons Attribution 4.0 InternationaliridiumN-heterocyclic carbeneamino acidasymmetric transfer hydrogenationDesign of Iridium N-Heterocyclic Carbene Amino Acid Catalysts for Asymmetric Transfer Hydrogenation of Aryl KetonesArticle - Refereed2021-05-24Catalystshttps://doi.org/10.3390/catal11060671