Pd-catalyzed asymmetric hydrogenation of alpha-fluorinated iminoesters in fluorinated alcohol: a new and catalytic enantioselective synthesis of fluoro alpha-amino acid derivatives.
[figure: see text] Under hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) promoted asymmetric hydrogenation of alpha-fluorinated iminoesters to afford highly enantioenriched beta-fluorinated alpha-amino esters. The yield and ee were much improved by employing fluorinated alcohols such as 2,2,2-trifluoroethanol (up to 91% ee).
Abe
H
H
Venture Business Laboratory, Graduate School of Natural Science and Technology, and Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushimanaka, Okayama 700-8530, Japan.
Amii
H
H
Uneyama
K
K
D000596:Amino Acids / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D010165:Palladium; D013237:Stereoisomerism; D014270:Trifluoroethanol / Q000737:chemistry
D000596:Amino Acids; D004952:Esters; D006845:Hydrocarbons, Fluorinated; D007097:Imines; D010165:Palladium; D014270:Trifluoroethanol; D006859:Hydrogen