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Unprecedented selectivity behaviour in the hydrogenation of an α,β-unsaturated ketone: hydrogenation of ketoisophorone over alumina-supported Pt and Pd

✍ Scribed by M von Arx; T Mallat; A Baiker

Publisher
Elsevier Science
Year
1999
Tongue
English
Weight
280 KB
Volume
148
Category
Article
ISSN
1381-1169

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✦ Synopsis

The partial hydrogenation of 2,6,6-trimethyl-2-cyclohexen-1,4-dione ketoisophorone was studied over alumina-supported Pt and Pd catalysts. The influence of solvent, pressure, catalyst pretreatment, and Lewis acid and base additives was investigated. Chemoselectivities over 90% were achieved in the saturation of the C5C or the sterically hindered C5O double bonds over Pt and Pd, respectively. This seems to be the first example for the selective reduction of an a ,b-unsaturated ketone to an unsaturated alcohol using dihydrogen. Enantioselective hydrogenation of the carbonyl group over cinchonidine-modified Pt afforded only 14% ee.

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