Meric, NerminKayan, CezmiGurbuz, NevinKarakaplan, MehmetBinbay, Nil ErtekinAydemir, Murat2024-08-042024-08-0420170957-4166https://doi.org/10.1016/j.tetasy.2017.10.004https://hdl.handle.net/11616/97999Metal-catalyzed asymmetric transfer hydrogenation is a powerful and practical method for the reduction of ketones to produce the corresponding secondary alcohols, which are valuable building blocks in the pharmaceutical, perfume, and agrochemical industries. Hence, a series of novel chiral beta-amino alcohols were synthesized by chiral amines with regioselective ring opening of (S)-propylene oxide or reaction with (S)-(+)-2-hydroxypropyl p-toluenesulfonate by a straightforward method. The chiral ruthenium catalytic systems generated from [Ru(arene)(mu-Cl)Cl](2) complexes and chiral phosphinite ligands based on amino alcohol derivatives were employed in asymmetric transfer hydrogenation of ketones to give the corresponding optically active alcohols; (2S)-1-([(2.9-2-[(diphenylphosphanypoxylpropyl][(1R)-1-phenylethyl]amino}propan-2-yldiphenylphosphinitobis[dichol-oro(eta(6)-benzene)ruthenium(II)] acts an excellent catalyst in the reduction of cl-naphthyl methyl ketone, giving the corresponding alcohol with up to 99% ee. The substituents on the backbone of the ligands were found to have a remarkable effect on both the conversion and enantioselectivity of the catalysts. Furthermore, this transfer hydrogenation is characterized by low reversibility under these conditions. (C) 2017 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccessAsymmetric Transfer HydrogenationDiels-Alder ReactionsAromatic KetonesPhosphinite LigandsCarbonyl-CompoundsHydride ComplexesOrganic-SynthesisCrystal-StructureAmino-AlcoholsAreneArticle28121739174910.1016/j.tetasy.2017.10.0042-s2.0-85031794388N/AWOS:000418988400009N/A