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Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with chiral water-soluble and heterogenized bifunctional catalysts of the RhCp*-type ligand
Authors:Barrón-Jaime Angélica  Narvaez-Garayzar Oscar F  González Jorge  Ibarra-Galván Valentín  Aguirre Gerardo  Parra-Hake Miguel  Chávez Daniel  Somanathan Ratnasamy
Institution:Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, Tijuana, Baja California, México.
Abstract:Asymmetric transfer hydrogenation (ATH) of prochiral aromatic ketones was carried out with a water-soluble complex of Rh(III)Cp* and mononitrobenzenesulfonamide bidentate ligand (1R,2R)-N-(2-aminocyclohexyl)-4-nitrobenzenesulfonamide 1 derived from chiral cyclohexane-1,2-diamine. Aqueous sodium formate was used as the hydride source. The reaction afforded the chiral alcohols in good enantioselectivities (79-93%) and yields (>99%). The modified monosulfonamide ligand was also covalently immobilized on solid phase such as silica, resin, and mesoporous SBA-15 silica and then explored as a catalyst with Rh(III)Cp* in the ATH of acetophenone.
Keywords:asymmetric transfer hydrogenation  aromatic ketones  chiral ligands  nitrobenzenesulfonamide  heterogenized ligands  RhIIICp*  SBA‐15
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