caa a22 4500 475760832 CHVBK 20180406123550.0 cr unu---uuuuu 170329e20000401xx s 000 0 eng 10.1007/BF02495491 doi (NATIONALLICENCE)springer-10.1007/BF02495491 Enantioselective hydrogenation of β-keto esters catalyzed by chiral binaphthylbisphosphine ruthenium complexes [Elektronische Daten] [V. Pavlov, E. Starodubtseva, M. Vinogradov, V. Ferapontov, O. Malyshev, G. Heise] The catalytic activity and the enantioselectivity manifested by cationic chiral binaphthylbisphosphine ruthenium complexes in asymmetric hydrogenation of β-keto esters were studied. The effects of the nature of the solvent, the reaction temperature, the pressure, addition of acids, and the reagent ratio on the yield and the degree of enantiomeric enrichment of the reaction products were examined. For hydrogenation of ethyl 4-chloroacetoacetate to form (R)- or (S)-enantiomers of ethyl 4-chloro-3-hydroxybutyrate, conditions were found which allow one to quantitatively prepare this valuable synthon with high enantiomeric purity (97-99%) at a low concentration of the catalyst (the ratio substrate: Ru=10000). Kluwer Academic/Plenum Publishers, 2000 hydrogenation nationallicence asymmetric catalysis nationallicence chiral bisphosphine ruthenium complexes nationallicence 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl nationallicence β-keto esters nationallicence ethyl 4-chloro-3-hydroxybutyrate nationallicence Pavlov V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Starodubtseva E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Vinogradov M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Ferapontov V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Malyshev O. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Heise G. Ohe Meadowlands Plaza, Cambrex Corporation, 07073, East Rutherford, NJ, USA aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/4(2000-04-01), 728-731 1066-5285 49:4<728 2000 49 11172 https://doi.org/10.1007/BF02495491 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495491 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Pavlov V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Starodubtseva E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Vinogradov M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Ferapontov V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Malyshev O. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Heise G. Ohe Meadowlands Plaza, Cambrex Corporation, 07073, East Rutherford, NJ, USA aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/4(2000-04-01), 728-731 1066-5285 49:4<728 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer