Tuesday, 24 May 2005

This presentation is part of: Graduate Posters

Asymmetric Transfer Hydrogenation of Allylic Compounds: a Novel Reaction with Homogeneous Chiral Ruthenium Catalysts

Marie G. Beauchamps and John Sowa Jr. Seton Hall University, South Orange, NJ

Asymmetric catalysis has been many chemists interest for its use in the preparation of chiral alcohols that are very important in the biological and pharmaceutical areas. There has been recent interest in asymmetric transfer hydrogenation (ATH) reactions that avoid gaseous hydrogen; the hydrogen source comes from solvent (isopropyl alcohol). Many examples of ATH of aldehydes and ketones have been reported but there has not been any report of this reaction for allylic alcohols. We were able to convert geraniol and gamma-geraniol to citronellol in 95% and 91% yield respectively using Ru-(S)-tol-binap as a chiral catalyst in the presence of KOH. The reaction with geraniol resulted in high enantiomeric excess (90% R), where gamma-geraniol resulted in 0% ee. The results of these reactions brought some insights for the mechanism of the ATH reaction and also encouraged us to apply this chemistry to a new class of substrates, allylic amines. Preliminary results of this new class of substrates will also be presented.

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