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By Ojima I.

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The high specificity of the catalyst for the hydrogenation of ketones has allowed unsaturated ketones to be reduced into chiral alcohols, leaving olefin functionalities intact. (i) Aromatic ketones Enantioselective hydrogenation of simple aromatic ketones has been studied with some chiral Rh, Ir, and Ru catalysts (Table 19). The DIOP–Rh290 and the DBPP–Rh291,291a complexes with a tertiary amine have been used in catalyzing the hydrogenation of acetophenone and moderate ee (80% and 87%, respectively) have been achieved.

With (EBTHI)TiH or (EBTHI)ZrH as the catalyst, a series of tri- or tetrasubstituted aryl alkenes have been hydrogenated with excellent enantioselectivity. Chiral cyclolanthanide complexes are also effective in the hydrogenation of 2-phenyl-1-butene at a low reaction temperature. 255 Cationic Ir-chiral N, P ligand complexes have recently shown promising results in the enantioselective hydrogenation of unfunctionalized olefins. Several chiral N,P ligands have been developed and have provided excellent ee in the asymmetric hydrogenation of 2-methyl stilbene, as shown in Table 9.

90 ð41Þ ð42Þ ð43Þ ð44Þ ð45Þ C–H Bond Formation by Asymmetric and Stereoselective Hydrogenation In contrast to successful results obtained with Ru catalysts, few systems have been reported on the Rh-catalyzed hydrogenation of , -unsaturated carboxylic acids. 79 The aminoalkyl side chain of the ligand is important to maintain the high reactivity and enantioselectivity. It is believed that the amino group of the ligand interacts with the carboxylic acid functionality of the substrate, hence facilitating the olefin coordination to the Rh center.

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Applications II. Transition Metal Compounds in Organic Synthesis 1 by Ojima I.

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