Abstract
The enantioselective hydrogenation of ethyl benzoylformate to (R)-ethyl mandelate over dihydrocinchonidine (DHCD)-modified Pt/Al2O3 catalyst in acetic acid was studied as a function of modifier concentration, hydrogen pressure and reaction temperature. The maximum enantioselectivity obtained under optimized conditions (DHCD concentration 1 mmol dm-3, 25 bar H2, 0 °C, AcOH/toluene 1:1) was 98% ee. The difference between the rates of racemic and enantioselective hydrogenation was less significant than in the case of ethyl pyruvate. This indicates that the high reaction rate in the enantioselective heterogeneous hydrogenation of α-ketoesters is not a necessary condition of the chiral induction.
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Sutyinszki, M., Szöri, K., Felföldi, K. et al. Heterogeneous Asymmetric Reactions. 29. Enantioselective Hydrogenation of Ethyl Benzoylformate over Dihydrocinchonidine-Modified Platinum–Alumina Catalyst in Acetic Acid. Catalysis Letters 81, 281–284 (2002). https://doi.org/10.1023/A:1016557929722
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DOI: https://doi.org/10.1023/A:1016557929722