Journal
CATALYSIS COMMUNICATIONS
Volume 8, Issue 8, Pages 1239-1243Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.catcom.2006.11.014
Keywords
enantioselective hydrogenation; isophorone; Pd catalysts; proline; kinetic resolution
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Enantioselective hydrogenation of isophorone (3,5,5-trimethyl-2-cyclohexenone) over (S)-proline modified Pd catalysts has been studied. Both the Pd particle size and the acid-base properties of the support influenced the hydrogenation reaction of isophorone and the subsequent kinetic resolution of 3,3,5-trimethylcyclohexanone (TMCH). This was explained by assuming the reaction pathway as a consequential process. The rapid hydrogenation of isophorone initially yielded racemic TMCH, and then the slow kinetic resolution consumed the (R)-TMCH, leaving (S)-TMCH in excess. Most promisingly, the Pd/MgO catalyst with enhanced adsorption of proline and moderate Pd particle sizes resulted in high enantioselectivity (ee of 95%) and 43% yield of TMCH. (c) 2006 Elsevier B.V. All rights reserved.
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