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Whereas the Pd-catalyzed hydrogenolysis of racemic 2-methyl-2-benzyloxycarbonyl-1-indanone in the presence of an unichiral (enantiopure) aminoalcohol leads to optically active 2methylindanone, such a domino reaction using optically active 2-methyl-2-benzyloxycarbonyl-1indanone and an achiral aminoalcohol affords racemic 2-methylindanone. According to these results, the ketone is obtained from the aminoalcohol-mediated protonation of an enolic species.

On the mechanism of the domino reaction of 2-methyl-2-benzyloxycarbonyl-1-indanone mediated by palladium, hydrogen and aminoalcohols