Russian Chemical Bulletin

, Volume 54, Issue 10, pp 2374–2378

Enantioselective hydrogenation of levulinic acid esters in the presence of the RuII-BINAP-HCl catalytic system

  • E. V. Starodubtseva
  • O. V. Turova
  • M. G. Vinogradov
  • L. S. Gorshkova
  • V. A. Ferapontov
Article

DOI: 10.1007/s11172-006-0125-2

Cite this article as:
Starodubtseva, E.V., Turova, O.V., Vinogradov, M.G. et al. Russ Chem Bull (2005) 54: 2374. doi:10.1007/s11172-006-0125-2

Abstract

The rate of hydrogenation of γ-ketoesters MeCOCH2CH2COOR (R = Et, Pri, But) in the presence of the chiral RuII—BINAP catalyst (BINAP is 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) greatly increases upon the addition of 5–10 equivalents of HCl with respect to ruthenium. In the hydrogenation of ethyl levulinate, the optically active γ-hydroxy ester initially formed would cyclize by ∼95% to give γ-valerolactone with optical purity of 98–99% ee. When the Ru(COD)(MA)2—BINAP—HCl catalytic system is used (COD is 1,5-cyclooctadiene, MA is 2-methylallyl), complete conversion of the ketoester (R = Et) in EtOH is attained in 5 h at 60 °C under an H2 pressure of 60–70 atm.

Key words

enantioselective catalytic hydrogenation ruthenium(II2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) esters of levulinic acid esters of γ-hydroxyvaleric acid optically active γ-valerolactone 

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • E. V. Starodubtseva
    • 1
  • O. V. Turova
    • 1
  • M. G. Vinogradov
    • 1
  • L. S. Gorshkova
    • 1
  • V. A. Ferapontov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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