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Asymmetric synthesis of heteroorganic analogs of natural compounds. 2. A convenient preparative method for the synthesis of enantiomerically pure (S)-(-)-o-, m-, and p-fluorophenylalanines and their 2-methylsubstituted analogs

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

Abstract

A convenient preparative method for the synthesis of the enantiomerically pure o-, m-, and p-fluorophenylalanines and their α-methyl-substituted analogs by means of the alkylation with the corresponding fluorine-containing benzyl chlorides of glycine and alanine in the Ni(II)-complexes of their Schiff bases with (S)-2-N(N′-benzylprolyl)aminobenzophenone is proposed.

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Literature cited

  1. R. A. Wildes, Austral. J. Plant Physiol.,2, 659 (1975), D. N. Wheatley and J. Y. Henderson, Nature,247, 286 (1974); S. L. C. Woo and Gillam, Biochem. J.,139, 741 (1974); J. Shiio and S. Suqimoto, Agr. Biol. Chem.,139, 627 (1975); M. Hennecke and A. Bock, Eur. J. Biochem.,55, 431 (1975); W. Biehn, Phytopathology,63, 421 (1973); W. N. Poillon, Biochemistry,21, 1400 (1982); Th. T. Otani and M. R. Brileg, J. Pharm. Sci.,74, 40 (1984).

    Google Scholar 

  2. J. J. Nestor, R. Tahilramani, T. L. Ho, et al., J. Med. Chem.,27, 1170 (1984).

    Google Scholar 

  3. K. Folkers, C. U. Bowers, T. Kubiak, and J. Stepinski, Z. Naturforsch.,39b, 528 (1984),

    Google Scholar 

  4. W. D. Kingsbury, J. Med. Chem.,26, 1725 (1983).

    Google Scholar 

  5. P. Cachia, B. D. Sykos, and R. S. Hodges, Biochemistry,22, 4145 (1983).

    Google Scholar 

  6. H. R. Bosshard and A. Berger, Helv. Chim. Acta,56, 1838 (1973).

    Google Scholar 

  7. E. L. Bennett and C. Niemann, J. Am. Chem. Soc,72, 1800 (1950).

    Google Scholar 

  8. I. H. Tong, C. Petitclerc, A. D'Iorio, and N. L. Benoiton, Can. J. Biochem.,49, 877 (1971).

    Google Scholar 

  9. H. Tanaka, K. Uchida, and M. Yamabe, J. Fluorine. Chem.,35, 253 (1987).

    Google Scholar 

  10. L. F. Godunova, E. I. Karpieskaya, E. S. Levitina, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1359 (1987).

    Google Scholar 

  11. D. Seebach and R. Naef, FRG Pat. No. 334,855, R. Zh. Khim., 9029P (1986).

  12. Yu. N. Belokon', A. G. Bulichev, V. I. Bachmutov, et al., J. Am. Chem. Soc,107, 4252 (1985).

    Google Scholar 

  13. Yu. N. Belokon', N. I. Chernoglazova, V. I. Vakhmutov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2798 (1987).

    Google Scholar 

  14. Yu. N. Belokon', N. I. Chernoglazova, K. A. Kochetkov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 803 (1984).

    Google Scholar 

  15. A. Gordon and R. Ford, A Chemist's Companion, Wiley, New York (1973).

    Google Scholar 

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Authors and Affiliations

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

    V. A. Soloshonok, Yu. N. Belokon', V. P. Kukhar', N. I. Chernoglazova, M. B. Saporovskaya, V. I. Bakhmutov, M. T. Kolycheva & V. M. Belikov

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

    V. A. Soloshonok, Yu. N. Belokon', V. P. Kukhar', N. I. Chernoglazova, M. B. Saporovskaya, V. I. Bakhmutov, M. T. Kolycheva & V. M. Belikov

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  1. V. A. Soloshonok
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  2. Yu. N. Belokon'
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  3. V. P. Kukhar'
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  4. N. I. Chernoglazova
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  5. M. B. Saporovskaya
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  6. V. I. Bakhmutov
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  7. M. T. Kolycheva
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  8. V. M. Belikov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1630–1636, July, 1990.

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Soloshonok, V.A., Belokon', Y.N., Kukhar', V.P. et al. Asymmetric synthesis of heteroorganic analogs of natural compounds. 2. A convenient preparative method for the synthesis of enantiomerically pure (S)-(-)-o-, m-, and p-fluorophenylalanines and their 2-methylsubstituted analogs. Russ Chem Bull 39, 1479–1485 (1990). https://doi.org/10.1007/BF00957865

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  • DOI: https://doi.org/10.1007/BF00957865

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