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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

1999; Elsevier BV; Volume: 148; Issue: 1-2 Linguagem: Inglês

10.1016/s1381-1169(99)00162-4

1873-314X

Matthias von Arx, Tamás Mallát, Alfons Baiker,

Surface Chemistry and Catalysis

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 CC or the sterically hindered CO double bonds over Pt and Pd, respectively. This seems to be the first example for the selective reduction of an α,β-unsaturated ketone to an unsaturated alcohol using dihydrogen. Enantioselective hydrogenation of the carbonyl group over cinchonidine-modified Pt afforded only 14% ee.