134ChemInform Abstract The asymmetric hydrogenation of the prochiral double bond in α-phenylcinnamic acid derivatives such as (I) on a modified Raney Ni catalyst is investigated. High enantioselectivity is observed in the conversion of compound (Ia) to (IIa).
081ChemInform Abstract Hydrogenation of the ketones (I) with an unmodified Raney-Ni catalyst leads to the cis-and trans-alcohols (II) and (III) with only low diastereoselectivities. In the presence of (R,R)-tartaric acid (RRTA), high diastereoselectivities and 10-15% enantioselectivity are observed for the ester ketones (Ia) and (Ib), while no change in diastereoselectivity and no enantioselectivity are observed for (Ic). The ester group in the β-position to the carbonyl group has a definite role in the formation of a H-bond between the substrate and the adsorbed tartaric acid, and hence in the enantioselectivity.
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