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.
Haraguchi
Naoki
N
Department of Materials Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi, Aichi 441-8580, Japan. haraguchi@tutms.tut.ac.jp
Tsuru
Keiichi
K
Arakawa
Yukihiro
Y
Itsuno
Shinichi
S
D002384:Catalysis; D002621:Chemistry / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008670:Metals; D008956:Models, Chemical; D011108:Polymers / Q000737:chemistry; D011137:Polystyrenes / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D003432:Cross-Linking Reagents; D007097:Imines; D008024:Ligands; D008670:Metals; D011108:Polymers; D011137:Polystyrenes; D012997:Solvents; D014867:Water; D012428:Ruthenium; D006859:Hydrogen