Asymmetric transfer hydrogenation of imines catalyzed by a polymer-immobilized chiral catalyst.

The asymmetric transfer hydrogenation of imines was performed with the use of a polymer-immobilized chiral catalyst. The chiral catalyst, prepared from crosslinked polystyrene-immobilized chiral 1,2-diamine monosulfonamide, was effective in the asymmetric transfer hydrogenation of N-benzyl imines in CH(2)Cl(2) to give a chiral amine in high yield and good enantioselectivity. Furthermore, an amphiphilic polymeric catalyst prepared from crosslinked polystyrene containing sulfonated groups successfully catalyzed the asymmetric transfer hydrogenation of cyclic imines in water. Enantioenriched secondary amines with up to 94% ee were obtained by using a polymeric catalyst.

[1]  S. Itsuno,et al.  Asymmetric Transfer Hydrogenation of Aromatic Ketones in Water using a Polymer‐Supported Chiral Catalyst Containing a Hydrophilic Pendant Group , 2008 .

[2]  J. Ying,et al.  Asymmetric transfer hydrogenation over Ru-TsDPEN catalysts supported on siliceous mesocellular foam. , 2007, Chemical communications.

[3]  J. Canivet,et al.  Water-soluble arene ruthenium catalysts containing sulfonated diamine ligands for asymmetric transfer hydrogenation of α-aryl ketones and imines in aqueous solution , 2007 .

[4]  Hua-Wei Zhang,et al.  Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water , 2007 .

[5]  S. Itsuno,et al.  Polymer-Supported Chiral Catalysts for Asymmetric Reactions in Water , 2006 .

[6]  S. Itsuno,et al.  Design of novel polymer-supported chiral catalyst for asymmetric transfer hydrogenation in water , 2006 .

[7]  Fei Wang,et al.  Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water. , 2006, Chemical communications.

[8]  J. Canivet,et al.  Water‐Soluble Arene Ruthenium Complexes Containing a trans‐1,2‐Diaminocyclohexane Ligand as Enantioselective Transfer Hydrogenation Catalysts in Aqueous Solution , 2005 .

[9]  Fan Wu,et al.  First example of asymmetric transfer hydrogenation in water induced by a chiral amino alcohol hydrochloride , 2005 .

[10]  Fei Wang,et al.  Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles. , 2005, The Journal of organic chemistry.

[11]  T. Ikariya,et al.  A remarkably effective catalyst for the asymmetric transfer hydrogenation of aromatic ketones in water and air. , 2005, Chemical communications.

[12]  Quanrui Wang,et al.  Preparation of polymer-supported Ru-TsDPEN catalysts and use for enantioselective synthesis of (S)-fluoxetine. , 2005, Organic & biomolecular chemistry.

[13]  J. Canivet,et al.  Cationic arene ruthenium complexes containing chelating 1,10-phenanthroline ligands , 2005 .

[14]  Jianliang Xiao,et al.  Asymmetric transfer hydrogenation in water with a supported Noyori-Ikariya catalyst. , 2004, Organic letters.

[15]  Jianliang Xiao,et al.  Accelerated asymmetric transfer hydrogenation of aromatic ketones in water. , 2004, Organic and biomolecular chemistry.

[16]  X. Cui,et al.  Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand. , 2003, Organic letters.

[17]  J. Henschke,et al.  Enantioselective Hydrogenation of Imines Using a Diverse Library of Ruthenium Dichloride(diphosphine)(diamine) Precatalysts , 2003 .

[18]  N. Leadbeater,et al.  Preparation of polymer-supported ligands and metal complexes for use in catalysis. , 2002, Chemical reviews.

[19]  A. Chan,et al.  Recoverable catalysts for asymmetric organic synthesis. , 2002, Chemical reviews.

[20]  Y. Chung,et al.  Use of surfactants in water-soluble ruthenium(II) complex-catalyzed asymmetric hydrogen-transfer reduction of aromatic ketones , 2002 .

[21]  H. Rhyoo,et al.  The first Ru(II)-catalysed asymmetric hydrogen transfer reduction of aromatic ketones in aqueous media. , 2001, Chemical communications.

[22]  Y. Chung,et al.  Use of amino amides derived from proline as chiral ligands in the ruthenium(II)-catalyzed transfer hydrogenation reaction of ketones , 2001 .

[23]  S. Brown,et al.  Efficient rhodium and iridium-catalysed asymmetric transfer hydrogenation using water-soluble aminosulfonamide ligands , 2001 .

[24]  S. Brown,et al.  Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation , 2001 .

[25]  H. Ishitani,et al.  Catalytic enantioselective addition to imines. , 1999, Chemical reviews.

[26]  M. Lemaire,et al.  Heterogeneous Enantioselective Catalytic Reduction of Ketones , 1997 .

[27]  J. G. Vries,et al.  Influence of degree of sulfonation of BDPP upon enantioselectivity in rhodium-BDPP catalyzed hydrogenation reactions in a two phase system , 1997 .

[28]  T. Ikariya,et al.  Asymmetric Transfer Hydrogenation of Imines , 1996 .

[29]  T. Ikariya,et al.  Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by Chiral Ruthenium(II) Complexes , 1995 .

[30]  J. G. Vries,et al.  Improving Enantioselectivity by Using a Mono-Sulphonated Diphosphine as Ligand for Homogeneous Imine Hydrogenation , 1992 .

[31]  J. Bakos,et al.  Rhodium(I)-sulfonated-bdpp catalysed asymmetric hydrogenation of imines in aqueous-organic two-phase solvent systems , 1991 .

[32]  J. Bakos,et al.  Chiral sulfonated phosphines. Syntheses and use as ligands in asymmetric hydrogenation using an aqueous-organic two-phase solvent system , 1989 .

[33]  M. Sekiya,et al.  Vapor-Liquid Equilibrium for Formic Acid-Triethylamine System Examined by the Use of a Modified Still. Formic Acid-Trialkylamine Azeotropes , 1977 .

[34]  K. Wagner.  Reactions with Addition Compounds Containing Activated Formic Acid , 1970 .