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Asymmetric hydrogen-transfer hydrogenation on rhodium(I) complexes with new optically active salen ligands derived from (4S,5S)-4,5-bis(aminomethyl)-2,2-dimethyl-1,3-dioxolane

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Abstract

New optically active C 2-symmetric salen-type ligands were synthesized on the basis of (4S,5S)-4,5-bis(aminomethyl)-2,2-dimethyl-1,3-dioxolane. These ligands were used to obtain cationic (trifluoromethanesulfonate) and neutral (chloride) rhodium(I) complexes with [(4S,5S)-2,2-dimethyl-5-{[(E)-pyridin-2-ylmethylidene]aminomethyl}-1,3-dioxolan-4-yl]-N-[(E)-pyridin-2-ylmethylidene]methanamine and [2,2-dimethyl-5-{[(E)-quinolin-2-ylmethylidene]aminomethyl}-1,3-dioxolan-4-yl]-N-[(E)-quinolin-2-ylmethylidene] methanamine. The latter complex ensured preparation of (S)-2-phenylethanol with an optical yield of 34.8% by transfer hydrogenation of acetophenone.

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Authors and Affiliations

  1. Irkutsk State Technical University, ul. Lermontova 83, Irkutsk, 664074, Russia

    L. O. Nindakova, N. M. Badyrova & F. M. Lebed’

  2. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    B. A. Shainyan

Authors
  1. L. O. Nindakova
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  2. B. A. Shainyan
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  3. N. M. Badyrova
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  4. F. M. Lebed’
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Corresponding author

Correspondence to L. O. Nindakova.

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Original Russian Text © L.O. Nindakova, B.A. Shainyan, N.M. Badyrova, F.M. Lebed’, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 1, pp. 65–69.

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Nindakova, L.O., Shainyan, B.A., Badyrova, N.M. et al. Asymmetric hydrogen-transfer hydrogenation on rhodium(I) complexes with new optically active salen ligands derived from (4S,5S)-4,5-bis(aminomethyl)-2,2-dimethyl-1,3-dioxolane. Russ J Org Chem 48, 59–63 (2012). https://doi.org/10.1134/S1070428012010083

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  • DOI: https://doi.org/10.1134/S1070428012010083

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