Advertisement

Enantioselective synthesis of nonproteinogenic amino acids

Conference paper
  • 638 Downloads
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 109)

Keywords

Amino Acid Ester Alkylation Product Proteinogenic Amino Acid Chiral Auxiliary Enantioselective Synthesis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

7 References

  1. 1.
    Rando, R. R.: Acc. Chem. Res. 8, 281 (1975); Abeles, R. H., Maycock, A. L.: ibid. 9, 313 (1976); Abeles, R. H.: Pure & Appl. Chem. 53, 149 (1980); Trowitzsch, W., Sahm, H.: Z. Naturforsch., Teil C 32, 78 (1977)CrossRefGoogle Scholar
  2. 2.
    Nass, G., Poralla, K., Zähner, H.: Naturwissenschaften 58, 603 (1971)CrossRefPubMedGoogle Scholar
  3. 3.
    Bell, E. A.: Endeavour 4, 102 (1980)CrossRefGoogle Scholar
  4. 4.
    Recent reviews on asymmetric synthesis, including amino acids ApSimon, J. W., Seguin, R. P.: Tetrahedron 35, 2797 (1979); Weinges, K., Stemmle, B.: Recent Develop. Chem. Nat. Carbon Compd. 7, 91 (1976); Valentine jr., D., Scott, J. W.: Synthesis 1978, 329; Kagan, H. B.: Pure & Appl. Chem. 43, 401 (1975)CrossRefGoogle Scholar
  5. 5.
    Morrison, J. D., Mosher, H. S.: Asymmetric Organic Reactions, 1. Aufl., Prentice Hall, Englewood Cliffs 1971Google Scholar
  6. 6.
    Schöllkopf, U. et al.: Angew. Chem. 90, 136 (1978); Angew. Chem. Int. Ed. Engl. 17, 117 (1978); Schöllkopf, U. et al.: Liebigs Ann. Chem. 1981, 439Google Scholar
  7. 7.
    Cf. Pankaskie, M., Abdel-Monem, M.: J. Med. Chem. 23, 121 (1980)CrossRefPubMedGoogle Scholar
  8. 8.
    Jung, G., Brückner, H., Schmitt, H.: in (Voelter, W., Weitzel, G., Eds.) Structure and Activity of Natural Peptides, 1981, 75, Walter de Gruyter, Berlin 1981Google Scholar
  9. 9.
    Schöllkopf, U. et al.: Liebigs Ann. Chem. 1981, 696Google Scholar
  10. 10.
    Cf. Blake, K. W., Porter, A. E. A., Sammes, P. G.: J. Chem. Soc. Perkin I 1972, 2494Google Scholar
  11. 11.
    Cf. Schmidt, R. R.: Angew. Chem. 87, 603 (1975); Angew. Chem. Int. Ed. Engl. 14, 581 (1975)Google Scholar
  12. 12.
    Weinges, K. et al.: Chem. Ber. 104, 3594 (1971). See this paper for alternative asymmetric syntheses of α-methyl amino acids as well as Kolb, M., Barth, J.: Tetrahedron Lett. 1979, 2999; Suzuki, M. et al.: Chem. Ind. (London) 1972, 687Google Scholar
  13. 13.
    Schöllkopf, U., Groth, U., Hartwig, W.: Liebigs Ann. Chem. 1981, 2407Google Scholar
  14. 14.
    This alternative model is analogous to the one proposed for the aldol addition. Cf. Kleschick, W. A., Buse, C. T., Heathcock, C. H.: J. Am. Chem. Soc. 99, 247 (1977); Buse, C. T., Heathcock, C. H.: ibid. 99, 8109 (1977); Fellmann, P., Dubois, J.-E.: Tetrahedron 34, 1349 (1978); House, H. O., Crumrine, D. S., Teranishi, A. Y., Olmstead, H. D.: J. Am. Chem. Soc. 95, 3310 (1973). Very likely, in the “real” transition state both factors, (HOMO)-LUMO) attraction and lithium complexation play a role.CrossRefGoogle Scholar
  15. 15.
    Schöllkopf, U. et al.: Synthesis 1981, 969. For an alternative synthesis of amino acids NCAs with trichlormethyl chloroformate instead of phosgene cf. Oya, M., Katakai, R., Nakai, H.: Chem. Lett. 1973, 1143Google Scholar
  16. 16.
    Schöllkopf, U., Groth, U., Deng, C.: Angew. Chem. 93, 793 (1981), Angew. Chem. Int. Ed. Engl. 20, 798 (1981)Google Scholar
  17. 17.
    Groth, U.: Dissertation, Univ. of Göttingen 1981Google Scholar
  18. 18.
    Schöllkopf, U., Neubauer, J.: Synthesis 1982, 861Google Scholar
  19. 19.
    Schöllkopf, U. et al.: Synthesis 1981, 966Google Scholar
  20. 20.
    Kehne, H.: Dissertation, Univ. of Göttingen 1980Google Scholar
  21. 21.
    Dauben, W. G., Fonken, G. J., Noyce, D. S.: J. Am. Chem. Soc. 78, 2579 (1956)CrossRefGoogle Scholar
  22. 22.
    Lonsky, R.: Diplomarbeit, Univ. of Göttingen 1980Google Scholar
  23. 23.
    Groth, U., Schöllkopf, U., Chiang, Y.: Synthesis 1982, 864Google Scholar
  24. 24.
    Westphalen, K.-O.: Dissertation, Univ. of Göttingen, presumably 1983Google Scholar
  25. 25.
    Nozulak, J.: Dissertation, Univ. of Göttingen, presumably 1983Google Scholar
  26. 26.
    We recently learned, that tert-leucine can in fact be obtained in almost optically pure form by enzymatic resolution. Sauber, K.: Hoechst AG, Pharmaforschung, private communicationGoogle Scholar
  27. 27.
    Cf. argumentation in ref. 13)Google Scholar
  28. 28.
    Schöllkopf, U., Groth, U.: Angew. Chem. 93, 1022 (1981); Angew. Chem. Int. Ed. Engl. 20, 977 (1981)Google Scholar
  29. 29.
    Chari, R. V. J., Wemple, J.: Tetrahedron Lett. 1979, 111Google Scholar
  30. 30.
    Schöllkopf, U., Nozulak, J., Groth, U.: Synthesis 1982, 868; this paper also describes the synthesis of 49 from 37aGoogle Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  1. 1.Institut für Organische Chemie der UniversitätGöttingenFRG

Personalised recommendations