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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
Author(s) -
BarrónJaime Angélica,
NarvaezGarayzar Oscar F.,
González Jorge,
IbarraGalván Valentín,
Aguirre Gerardo,
ParraHake Miguel,
Chávez Daniel,
Somanathan Ratnasamy
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20902
Subject(s) - chemistry , acetophenone , transfer hydrogenation , sodium formate , bifunctional , ligand (biochemistry) , catalysis , enantioselective synthesis , denticity , chirality (physics) , chiral ligand , diamine , organic chemistry , asymmetric hydrogenation , aqueous solution , mesoporous silica , polymer chemistry , medicinal chemistry , mesoporous material , ruthenium , crystal structure , quantum mechanics , biochemistry , nambu–jona lasinio model , receptor , chiral symmetry breaking , physics , quark
Asymmetric transfer hydrogenation (ATH) of prochiral aromatic ketones was carried out with a water‐soluble complex of Rh III Cp* and mononitrobenzenesulfonamide bidentate ligand (1 R ,2 R )‐ 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. Chirality, 2011. © 2010 Wiley‐Liss, Inc.
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