New methodologies for the synthesis of compound libraries

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Shū Kobayashi


Abstract

New methodologies for the synthesis of compound libraries are discussed. They are based on new carbon–carbon bond-forming reactions on the solid-phase (using polymer-supported silyl enol ethers), library preparation using polymer catalysts, and multi-component reactions in liquid phase. Development of new linker resins for efficient reactions on the solid-phase and a new method for the synthesis of monosaccharide libraries are also described.


References

  1. L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555 CrossRef CAS and references cited therein.
  2. S. Kobayashi, I. Hachiya, S. Suzuki and M. Moriwaki, Tetrahedron Lett., 1996, 37, 2809 CrossRef CAS.
  3. S. Kobayashi, M. Araki and M. Yasuda, Tetrahedron Lett., 1995, 36, 5773 CrossRef CAS and references cited therein.
  4. S. Kobayashi, H. Ishitani and S. Nagayama, Synthesis, 1995, 1195 CrossRef CAS.
  5. I. Ugi, A. Dömling and W. Hörl, Endeavour, 1994, 18, 115 CrossRef CAS.
  6. R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown and T. A. Keating, Acc. Chem. Res., 1996, 29, 123 CrossRef CAS.
  7. P. A. Tempest, S. D. Brown and R. W. Armstrong, Angew. Chem., Int. Ed. Engl., 1996, 35, 640 CrossRef CAS.
  8. S. Kobayashi, M. Moriwaki, R. Akiyama, S. Suzuki and I. Hachiya, Tetrahedron Lett., 1996, 37, 7783 CrossRef CAS.
  9. T. Mukaiyama, K. Banno and K. Narasaka, Chem. Lett., 1973, 1101.
  10. S. Kobayashi, I. Hachiya, H. Ishitani and M. Araki, Synlett, 1993, 472 CrossRef CAS.
  11. S. Kobayashi, I. Hachiya and M. Yasuda, Tetrahedron Lett., 1996, 37, 5569 CrossRef CAS.
  12. M. J. Kurth, L. A. Ahlberg Randall, C. Chen, C. Melander, R. B. Miller, K. McAlister, G. Reitz, R. Kang, T. Nakatsu and C. Green, J. Org. Chem., 1994, 59, 5862 CrossRef CAS.
  13. K. Narasaka, K. Soai and T. Mukaiyama, Chem. Lett., 1974, 1223 CAS.
  14. S. Kobayashi, R. Akiyama, T. Furuta and M. Moriwaki, Molecules Online, 1998, 2, 35 CrossRef CAS.
  15. (a) L. F. Tietze and A. Steinmetz, Angew. Chem., Int. Ed. Engl., 1996, 35, 651 CAS; (b) S. M. Hutchins and K. T. Chapman, Tetrahedron Lett., 1996, 37, 4869 CrossRef CAS.
  16. S. Kobayashi and M. Moriwaki, Tetrahedron Lett., 1997, 38, 4251 CrossRef CAS.
  17. For leading references, see (a) Trends in Synthetic Carbohydrate Chemistry, eds. D. Horton, L. D. Hawkins and G. McGarvey, ACS Symposium Series 386, Amrican Chemical Society, Washington, DC, 1989 Search PubMed; (b) T. Kawano, J. Cui, Y. Koezuka, I. Toura, Y. Kaneko, K. Motoki, H. Ueno, R. Nakagawa, H. Sato, E. Kondo, H. Koseki and M. Taniguchi, Science, 1997, 278, 1626 CrossRef CAS and references cited therein.
  18. For example, (a) N. Prentice, L. J. Cundet and F. Smith, J. Am. Chem. Soc., 1956, 78, 4439 CrossRef CAS; (b) R. Kuhn and G. Baschang, Liebigs Ann. Chem., 1960, 636, 164 Search PubMed.
  19. For example, (a) G. J. McGarvey, M. Kimura and T. Oh, J. Carbohydr. Chem., 1984, 3, 125 CAS; (b) T. Mukaiyama, K. Suzuki, T. Yamada and F. Tabusa, Tetrahedron, 1990, 46, 265 CrossRef CAS.
  20. For example, S. J. Danishefsky and M. P. DeNinno, in Trends in Synthetic Carbohydrate Chemistry, eds. D. Horton, L. D. Hawkins and G. McGarvey, ACS Symposium Series 386, American Chemical Society, Washington, DC, 1989, pp. 176–181 Search PubMed.
  21. (a) S. Y. Ko, W. M. Lee, S. Masamune, L. A. Reed, III, K. B. Sharpless and F. J. Walker, Tetrahedron, 1990, 46, 245 CrossRef CAS; (b) S. Kobayashi and T. Kawasuji, Synlett, 1993, 911 CrossRef.
  22. S. Kobayashi, T. Wakabayashi and M. Yasuda, J. Org. Chem., 1998, 63, 4868 CrossRef CAS.
  23. T. Mukaiyama, T. Yamada and K. Suzuki, Chem. Lett., 1983, 5 CAS.
  24. S. Kobayashi, Y. Fujishita and T. Mukaiyama, Chem. Lett., 1990, 1455 CAS.
  25. S. Kobayashi and M. Horibe, Chem. Eur. J., 1997, 3, 1472 CAS and references cited therein.
  26. S. Kobayashi and S. Nagayama, J. Org. Chem., 1996, 61, 2256 CrossRef CAS and references cited therein.
  27. S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 1996, 118, 8977 CrossRef CAS.
  28. We have found that lanthanide triflates (including scandium triflate) are water-tolerant Lewis acids and efficient catalysts in several synthetic reactions in aqueous media. (a) S. Kobayashi, Synlett, 1994, 689 CrossRef CAS; (b) S. Kobayashi, in Organic Reactions in Water, ed. P. Grieco, Chapman & Hall, London, 1997, and references cited therein Search PubMed.
  29. S. Kobayashi, S. Nagayama and T. Busujima, Tetrahedron Lett., 1996, 37, 9221 CrossRef CAS.
  30. S. Kobayashi, S. Komiyama and H. Ishitani, Biotechol. Bioeng., 1998, 1, 23 Search PubMed.
  31. For recent examples, (a) S. Kobayashi, T. Busujima and S. Nagayama, Chem. Commun., 1998, 19 RSC; (b) H. Oyamada and S. Kobayashi, Synlett, 1998, 249 CAS and references cited therein.
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