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Stereochemical control in reactions of chiral ketone with 2-lithiated substituted ferrocene derivatives

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Abstract

The formation of a new chiral center in the reactions of ketone 4-MeOC6H4CH(Et)C(O)Et with planar-chiral 2-lithio-1-methyl- and 1-chloro-2-lithioferrocenes proceeded stereoselectively to give two diastereomers in a ratio of ∼3 : 2 or a single diastereomer, respectively, out of four possible diastereomeric 4-aryl-3-ferrocenylhexan-3-ols. The replacement of the hydroxy group in the resulting compounds by hydrogen under the conditions of ionic hydrogenation was studied. The configurations of the reaction products were established by X-ray diffraction analysis and 1H NMR spectroscopy.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    L. L. Troitskaya, T. V. Demeshchik, S. T. Ovseenko, Z. A. Starikova & V. I. Sokolov

  2. Laboratory of Inorganic Chemistry and Molecular Materials, P. and M. Curie University, National Center for Scientific Research Unit, 7071, France, 4 pl. Jussieu, 75252 Paris, Bat. 42

    B. Malezieux & M. Gruselle

Authors
  1. L. L. Troitskaya
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  2. T. V. Demeshchik
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  3. S. T. Ovseenko
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  4. Z. A. Starikova
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  5. V. I. Sokolov
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  6. B. Malezieux
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  7. M. Gruselle
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Troitskaya, L.L., Demeshchik, T.V., Ovseenko, S.T. et al. Stereochemical control in reactions of chiral ketone with 2-lithiated substituted ferrocene derivatives. Russian Chemical Bulletin 52, 616–623 (2003). https://doi.org/10.1023/A:1023950505008

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  • DOI: https://doi.org/10.1023/A:1023950505008

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