Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with chiral water-soluble and heterogenized bifunctional catalysts of the RhCp*-type ligand.
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.
Barrón-Jaime
Angélica
A
Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, Tijuana, Baja California, México.
Narvaez-Garayzar
Oscar F
OF
González
Jorge
J
Ibarra-Galván
Valentín
V
Aguirre
Gerardo
G
Parra-Hake
Miguel
M
Chávez
Daniel
D
Somanathan
Ratnasamy
R
D000098:Acetophenones / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry; D000096926:Benzenesulfonamides
D000098:Acetophenones; D000438:Alcohols; D003510:Cyclohexanes; D008024:Ligands; D009942:Organometallic Compounds; D012238:Rhodium; D012822:Silicon Dioxide; D013449:Sulfonamides; D014867:Water; C557462:(1R,2R)-N-(2-aminocyclohexyl)-4-nitrobenzenesulfonamide; D000096926:Benzenesulfonamides; C509969:SBA-15