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Enantioselective hydrogen transfer hydrogenation on rhodium colloid systems with optically active stabilizers

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Abstract

Hydrogen transfer hydrogenation of acetophenone and methyl benzoylformate with 2-propanol was studied on colloidal systems obtained by reduction of rhodium complexes in the presence of optically active compounds: chiral diamines, quaternary salt (4S,5S)-(–)-N 1,N 4-dibenzylene-2,3-dihydroxy-N 1,N 1,N 4,N 4-tetramethylbutane-1,4-diammonium dichloride and (8S,9R)-(–)-cinchonidine. The increase in the molar ratio modifier/Rh leads to the increase in the enantioneric excess (ee) of the reaction products. The largest ee [43.8% of (R)-1-phenylethanol and 58.2% of methyl ester of (R)-mandelic acid] were achieved for the ratios (8S,9R)-(–)-cinchonadine: Rh = 9: 1 and 3: 1, respectively. The catalyst was characterized by the high-resolution transmission electron microscopy, X-ray diffraction analysis, and thermal analysis.

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Authors and Affiliations

  1. Irkutsk National Research Technical University, ul. Lermontova 83, Irkutsk, 664074, Russia

    L. O. Nindakova, N. M. Badyrova, V. V. Smirnov, V. O. Strakhov & S. S. Kolesnikov

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  1. L. O. Nindakova
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  2. N. M. Badyrova
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  3. V. V. Smirnov
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Original Russian Text © L.O. Nindakova, N.М. Badyrova, V.V. Smirnov, V.О. Strakhov, S.S. Kolesnikov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 6, pp. 909–918.

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Nindakova, L.O., Badyrova, N.M., Smirnov, V.V. et al. Enantioselective hydrogen transfer hydrogenation on rhodium colloid systems with optically active stabilizers. Russ J Gen Chem 86, 1240–1249 (2016). https://doi.org/10.1134/S1070363216060049

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