Heterogeneous asymmetric hydrogenation and deuteration of 2-methyl-2-pentenoic acid over Pd supported catalysts: proton/deuterium exchange

Add time:08/04/2019    Source:sciencedirect.com

The asymmetric hydrogenation of trans-2-methyl-2-pentenoic acid in hexane over two well defined E-40692 and E-5220 Engelhard Pd/Al2O3 catalysts modified with cinchonidine was re-examined, the literature results have been reproduced and it was found that the E-40692 catalyst lead to the best conversions and %e.e. Deuteration experiments have been conducted under identical (solvent, catalyst, constituents ratios and temperature) conditions: percentage of H/D exchange (in the starting substrate and in the saturated product) as well as percentage of deuteration at all carbons have been determined by 1H NMR and indicated that double bond migration and cis/trans isomerization occurred during hydrogenation/deuteration but that these processes contributed less at higher pressure (40 bar) and in the presence of cinchonidine.

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