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Borohydride reduction of acetophenone and esters of dehydrocarboxylic acids in the presence of chiral cobalt(II) diamine complexes

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Abstract

The catalytic reduction of acetophenone, methyl α-acetamidocinnamate, and dimethyl itaconate with alcohol-modified sodium borohydride was studied in the presence of complexes CoCl2·L2 (L2 are chiral C 2-symmetric diamines: (4S,5S)-2,2-dimethyl-4,5-bis(aminomethyl)-1,3-dioxolane, (4S, 5S)-2,2-dimethyl-4,5-bis(methylaminomethyl)-1,3-dioxolane, (4S, 5S)-2,2-dimethyl-4,5-bis(dimethylaminomethyl)-1,3-dioxolane, and (4S, 5S)-2,2-dimethyl-4,5-bis(diphenylaminomethyl)-1,3-dioxolane). The maximum enantiomeric excess of (S)-1-phenylethanol was 24%, that of dimethyl α-methylsuccinate was 38%.

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Authors and Affiliations

  1. A. E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 2 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    L. O. Nindakova & B. A. Shainyan

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  1. L. O. Nindakova
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  2. B. A. Shainyan
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 342–347, February, 2005.

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Nindakova, L.O., Shainyan, B.A. Borohydride reduction of acetophenone and esters of dehydrocarboxylic acids in the presence of chiral cobalt(II) diamine complexes. Russ Chem Bull 54, 348–353 (2005). https://doi.org/10.1007/s11172-005-0258-8

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  • DOI: https://doi.org/10.1007/s11172-005-0258-8

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