ASYMMETRIC CATALYSIS, .69. ENANTIOSELECTIVE HYDROGENATION OF DICARBONYL-COMPOUNDS WITH NICKEL-CATALYSTS MODIFIED WITH NABR/L-(+)-TARTARIC ACID

BRUNNER, H and AMBERGER, K and WISCHERT, T (1991) ASYMMETRIC CATALYSIS, .69. ENANTIOSELECTIVE HYDROGENATION OF DICARBONYL-COMPOUNDS WITH NICKEL-CATALYSTS MODIFIED WITH NABR/L-(+)-TARTARIC ACID. BULLETIN DES SOCIETES CHIMIQUES BELGES, 100 (8). pp. 585-595. ISSN 0037-9646,

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Abstract

Enantioselective hydrogenation of ethyl pyruvate BTSE to methyl lactate MSE, methyl acetoacetate AEME to methyl 3-hydroxybutanoate HBME, and 2,5-hexanedione Acyac to 5-hydroxy-2-hexanone HH and 2,5-hexanediol HD by NaBr/L-(+)-tartaric acid modified transition metal catalysts were carried out. Finely divided catalysts prepared by cocondensation of transition metals (Cr, Mn, Fe, Co, Ni), 4 different supported nickel catalysts (BaSO4, Al2O3, C, SiO2) and 3 Ni/Al alloys (2:1, 10:7, 1:1) were used in the enantioselective hydrogenation of AEME. Transition metals, Ni/Al alloys and supported nickel catalysts showed satisfactory enantioselectivity but had a low hydrogenation rate. Additionally, 20 nickel powders with different surface areas were tested. Low enantioselectivities were obtained in the hydrogenation of ethyl pyruvate and 2,5-hexanedione. In contrast, the beta-keto ester AEME was hydrogenated with high enantioselectivity (up to 68% ee). The best results were achieved using catalysts with a surface area between 4.1-7.5 m2/g.

Item Type: Article
Uncontrolled Keywords: ;
Depositing User: Dr. Gernot Deinzer
Last Modified: 19 Oct 2022 08:46
URI: https://pred.uni-regensburg.de/id/eprint/54929

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