Enantioselective hydrogenation of β-keto esters catalyzed by chiral binaphthylbisphosphine ruthenium complexes |
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| Authors: | V. A. Pavlov E. V. Starodubtseva M. G. Vinogradov V. A. Ferapontov O. R. Malyshev G. L. Heise |
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| Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(2) Ohe Meadowlands Plaza, Cambrex Corporation, 07073 East Rutherford, NJ, USA |
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| Abstract: | 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). Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 725–728, April. 2000. |
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| Keywords: | hydrogenation asymmetric catalysis chiral bisphosphine ruthenium complexes 2,2′ -bis(diphenylphosphanyl)-1,1′ -binaphthyl β -keto esters ethyl 4-chloro-3-hydroxybutyrate |
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