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Enantioselective Cathodic Hydrogenation of Prostereogenic Activated Double Bonds

  • M. F. Nielsen
  • B. Batanero
  • S. Rolvering
  • H. J. Schäfer
Conference paper

Abstract

4-Methylcoumarine (1) is enantioselectively reduced in the presence of yohimbine at pH = 3 to afford 4-methyldihydrocoumarine (2) in 61% yield and nearly 70% ee. With 3-methylindenone and strychnine the dihydroproduct is formed with up to 36% ee. The role of the alkaloids is to catalyze the tautomerization of an intermediate enol radical and to enantioselectively protonate a ketoanion.

Keywords

Quantum Chemical Calculation Aqueous Methanol Enantiomeric Excess Cathodic Reduction Aqueous Methanol Solution 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • M. F. Nielsen
    • 2
  • B. Batanero
    • 1
  • S. Rolvering
    • 1
  • H. J. Schäfer
    • 1
  1. 1.Organisch-Chemisches InstitutUniversität MünsterMünsterGermany
  2. 2.Department of Chemistry, The H.C. Orsted InstituteUniversity of CopenhagenCopenhagen 0Denmark

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