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Asymmetric synthesis of heteroorganic analogs of natural compounds. 4. Diastereo- and enantioselective synthesis of (2s, 3s)-4,4,4-trifluorothreonine and (2s, 3s)-β-perfluoroalkylserines

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

Perfluorinated aliphatic aldehydes react with the Ni(II) complex of the glycine Schiff base with (S)-2-[N(N′-benzylprolyl)amino]benzophenone in the presence of MeONa to give (2S, 2S)-perfluoroalkylserines, while alkanals react to form (2R, 3S)-diastereomers.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petroleum Chemistry, Academy of Sciences of the Ukrainian SSR, Kiev

    V. A. Soloshonok, V. P. Kukhar', A. S. Batsanov, M. A. Galakhov, Yu. N. Belokon' & Yu. T. Struchkov

  2. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    V. A. Soloshonok, V. P. Kukhar', A. S. Batsanov, M. A. Galakhov, Yu. N. Belokon' & Yu. T. Struchkov

Authors
  1. V. A. Soloshonok
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  2. V. P. Kukhar'
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  3. A. S. Batsanov
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  4. M. A. Galakhov
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  5. Yu. N. Belokon'
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  6. Yu. T. Struchkov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1548–1554, July, 1991.

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Soloshonok, V.A., Kukhar', V.P., Batsanov, A.S. et al. Asymmetric synthesis of heteroorganic analogs of natural compounds. 4. Diastereo- and enantioselective synthesis of (2s, 3s)-4,4,4-trifluorothreonine and (2s, 3s)-β-perfluoroalkylserines. Russ Chem Bull 40, 1366–1372 (1991). https://doi.org/10.1007/BF00961234

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  • DOI: https://doi.org/10.1007/BF00961234

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