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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 4
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Original Articles

A New Approach to the Efficient Method for the Asymmetric Synthesis of (S)-O-, M-, P-Fluorophenylalanines and Their 2-Methyl-substituted Analogs

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Pages 493-506 | Received 29 Oct 2009, Published online: 02 Feb 2011

REFERENCES

  • Wildes, R. A., Pitman, M. G., Schaefer, N., Wheatley, D. N., Henderson, J. Y., Gillam, S. S., Woo, S. L. C., Woolf, L. I., Poillon, W. N., , 1975. Comparison of isomers of fluorophenylalanine as inhibitors of ion transport across barley roots, Austral. J. Plant Physiol. 2 (1975), pp. 659–661, (a), (b), (c), (d).
  • Bikshapathy, E., Sitaram, N., and Nagaranj, R., 1999. Effect of Introducing p-fluorophenylalanine and multiple tryptophan residues in a 13-residue antibacterial peptide, Protein Peptide Lett. 6 (1999), pp. 67–71.
  • Gullbo, J., Lindhagen, E., Bashir-Hassan, S., Tullberg, M., Ehrsson, H., Lewensohn, R., Nygren, P., Torre, M., Luthman, K., Larsson, R., Gullbo, J.Wallinder, C., Tullberg, M., Lövborg, H., Ehrsson, H., Lewensohn, R., Nygren, P., Luthman, K., Larsson, R., , 2004. Antitumor efficacy and acute toxicity of the novel dipeptide melphalanyl-p-L-fluorophenylalanine ethyl ester (J1) in vivo, Invest. New Drugs 22 (2004), pp. 411–420(a), (b).
  • Lourens, D. R., and Benett, P. N., 1993. Clinical Pharmacology. Moscow: Medicina; 1993.
  • Soloshonok, V. A., Belokon, Y. N., Kukhar, V. P., Chernoglazova, N. I., Saporovskaya, M. B., Bakhmutov, V. I., Kolycheva, M. T., and Belikov, V. M., 1990. Asymmetric synthesis of heteroorganic analogs of natural compounds: A convenient preparative method for the synthesis of enantiomerically pure (S)-(−)-o-, m-, and p-fluorophenylalanines and their 2-methylsubstituted analogs, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 7 (1990), pp. 1630–1636.
  • Belokon, Y. N., Soloshonok, V. A., Ohkura, H., Sorochinsky, A., Voloshin, N., Markovsky, A., Belik, M., Yamazaki, T., , 1992. Chiral complexes of Ni(II), Cu(II), and Cu(I) as reagents, catalysts and receptors for asymmetric synthesis and chiral recognition of amino acids, Pure Appl. Chem. 64 (1992), pp. 1917–1924(a), (b).
  • Belokon, Y. N., Maleev, V. I., Saporovskaya, M. B., Bakhmutov, V. I., Timofeeva, T. V., Batsanov, A. S., Struchkov, Y. T., Popkov, A., Gree, A., Nádvorník, M., and Lyčka, A.Belokon', Y. N., Maleev, V. I., Petrrosyan, A. A., Savel'eva, T. F., Ikonnikov, N. S., Peregudov, A. S., Khrustalev, V. N., Saghiyan, A. S., , 1988. Ni(II) complexes of Schiff's base of glycine and alanine with (S)-N-(α-naphtyl)proline derivatives for asymmetric synthesis of amino acids, Koordinats. Khim. 11 (1988), pp. 1565–1575(a), (b), (c).
  • Saghiyan, A. S., Dadayan, S. A., Petrosyan, S. G., Manasyan, L. L., Geolchanyan, A. V., Djamgaryan, S. M., Andreasyan, S. A., Maleev, V. I., and Khrustalev, V. N., 2006. New chiral NiII complexes of Schiff's bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids, Tetrahedron: Asymmetry 17 (2006), pp. 455–467.
  • Saghiyan, A. S., Manasyan, L. L., Dadayan, S. A., Petrosyan, S. G., Petrosyan, A. A., Maleev, V. I., and Khrustalev, V. N., 2006. Novel modified chiral NiII complexes with the Schiff bases of (E)- and (Z)-2-aminobut-2-enoic acids, Russ. Chem. Bull. Internat. Ed. 55 (2006), pp. 442–450.
  • Belokon, Y. N., Bulychev, A., Vitt, S., Struchkov, Y., Batsanov, A., Timofeeva, T., Tsyrypkin, V., Ryzhov, M., Lysova, L., Bakhmutov, V., Belikov, V., Belokon, Y. N., Saghyan, A. S., Djamgaryan, S. M., Bakhmutov, V. I., Vitt, S. V., Batsanov, A. S., and Struchkov, Y. T.Belikov, V. M., Saghyan, A. S., Geolchanyan, A. V., Petrosyan, S. G., Ghochikyan, T. V., Haroutunyan, V. S., Avetisyan, A. A., Belokon, Y. N., Fisher, F., , 1985. General method of diastereo- and enantioselective synthesis of β-hydroxy-α-amino acids by condensation of aldehydes and ketones with glycine, J. Am. Chem. Soc. 107 (1985), pp. 4252–4259, (a), (b), (c).

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