Counterattack reagents in organic synthesis: versatility and efficiency

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Jih Ru Hwu, Jih Ru Hwu and Shwu-Chen Tsay


Abstract

The concept of ‘counterattack reagents’ has been applied in the development of various chemical transformations. The use of counterattack reagents allows complicated reactions to be accomplished in a single flask without the isolation of intermediates. Thus multistep transformations can be simplified to ‘one-step’ operations. Representative examples of applications illustrated herein include oxidation, reduction, C–C single and double bond formation, cyclization, C–Si bond formation, O- and N-silylations and allylsilylation, as well as dealkylation. Comparisons are made between the results from traditional and ‘counterattack’ methods. Examples also include the utilization of ‘pseudo-counterattack’ and ‘intramolecular counterattack’ strategies in organic synthesis. The ‘counterattack reagents’ involved in those reactions are often, but not limited to, silicon-containing compounds.


References

  1. J. R. Hwu and B. A. Gilbert, Tetrahedron, 1989, 45, 1233 CrossRef CAS.
  2. J. R. Hwu, G. H. Hakimelahi, F. F. Wong and C. C. Lin, Angew. Chem., Int. Ed. Engl., 1993, 32, 608 CrossRef.
  3. J. R. Hwu, S.-C. Tsay, A. A. Moosavi-Movahedi and G. H. Hakimelahi, unpublished work.
  4. J. R. Hwu, T. Lee and B. A. Gilbert, J. Chem. Soc., Perkin Trans. 1, 1992, 3219 RSC.
  5. J. R. Hwu, J. A. Robl, N. Wang, D. A. Anderson, J. Ku and E. Chen, J. Chem. Soc., Perkin Trans. 1, 1989, 1823 RSC.
  6. J. R. Hwu and N. Wang, Tetrahedron, 1988, 44, 4181 CrossRef CAS.
  7. J. R. Hwu, L. C. Lin and B. R. Liaw, J. Am. Chem. Soc., 1988, 110, 7252 CrossRef CAS.
  8. J. R. Hwu and S.-C. Tsay, Tetrahedron, 1990, 46, 7413 CrossRef CAS.
  9. S.-C. Tsay, P. Gani and J. R. Hwu, J. Chem. Soc., Perkin Trans. 1, 1991, 1493 RSC.
  10. J. R. Hwu, D. A. Anderson, N. Wang, M. M. Buchner, P. Gani and S.-C. Tsay, Chem. Ber., 1990, 123, 1667 CAS.
  11. J. R. Hwu and S.-C. Tsay, J. Org. Chem., 1990, 55, 5987 CrossRef CAS.
  12. J. R. Hwu, J. Org. Chem., 1983, 48, 4432 CrossRef CAS.
  13. J. R. Hwu, N. Wang and R. T. Yung, J. Org. Chem., 1989, 54, 1070 CrossRef CAS.
  14. J. R. Hwu, J. Chem. Soc., Chem. Commun., 1985, 452 RSC.
  15. J. R. Hwu, S.-C. Tsay, N. Wang and G. H. Hakimelahi, Organometallics, 1994, 13, 2461 CrossRef CAS.
  16. W. Carruthers, Some Modern Methods of Organic Synthesis, Cambridge University Press, 3rd edn., 1986, p. 45 Search PubMed.
  17. E. J. Corey, D. Seebach and R. Freedman, J. Am. Chem. Soc., 1967, 89, 434 CrossRef CAS.
  18. P. F. Jones, M. F. Lappert and A. C. Szary, J. Chem. Soc., Perkin Trans. 1, 1973, 2272 RSC.
  19. F. Carey and A. S. Court, J. Org. Chem., 1972, 37, 1926 CrossRef CAS.
  20. C. A. Brown and A. Yamaichi, J. Chem. Soc., Chem. Commun., 1979, 100 RSC.
  21. J. R. Hwu and S.-C. Tsay, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, vol. 5, pp. 3436–3437 Search PubMed.
  22. O. Smrekar and U. Wannagat, Monatsh. Chem., 1969, 100, 760 CAS.
  23. R. West and P. Boudjouk, J. Am. Chem. Soc., 1973, 95, 3987 CrossRef CAS.
  24. Y. H. Chang, F.-T. Chiu and G. Zon, J. Org. Chem., 1981, 46, 342 CrossRef CAS.
  25. H.-P. Malach, R. Bussas and G. Kresze, Liebigs Ann. Chem., 1982, 7, 1384 Search PubMed and references cited therein.
  26. J. R. Dilworth, S. J. Harrison, R. A. Henderson and D. R. M. Walton, J. Chem. Soc., Chem. Commun., 1984, 176 RSC and references cited therein.
  27. K. Seppelt and W. Sundermeyer, Chem. Ber., 1969, 102, 1247 CAS.
  28. W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlag, 1983, ch. 11 Search PubMed.
  29. E. Colvin, Silicon in Organic Synthesis, Butterworths, Boston, 1981, ch. 9 Search PubMed.
  30. A. J. Mitchell, K. S. Murray, P. J. Newman and P. E. Clark, Aust. J. Chem., 1977, 30, 2439 CAS.
  31. W. Walter and E. Schaumann, Synthesis, 1971, 111 CrossRef CAS and references cited therein.
  32. M. H. Benn and M. G. Ettlinger, J. Chem. Soc., Chem. Commun., 1965, 445 RSC.
  33. M. Matsuo and E. W. Underhill, Biochem. Biophys. Res. Commun., 1969, 36, 18 CrossRef CAS.
  34. M. Matsuo and E. W. Underhill, Phytochemistry, 1971, 10, 2279 CrossRef CAS.
  35. Shell Internationale Research Maatschappij, N. V. Neth. Appl. 6 615 725/1967 (Chem. Abstr., 1968, 69, 35430s) Search PubMed.
  36. J. Myerson, W. F. Haddon and E. L. Soderstorm, Tetrahedron Lett., 1982, 23, 2757 CrossRef CAS.
  37. E. P. Lebedev, V. A. Baburina and V. O. Reikhsfel'd, J. Gen. Chem. USSR (Engl. Transl.), 1975, 45, 337.
  38. E. J. Hedgley and W. G. Overend, Chem. Ind. (London), 1960, 378 CAS.
  39. M. V. Bhatt and S. U. Kulkarni, Synthesis, 1983, 249 CrossRef CAS.
  40. M.-J. Shiao, W.-S. Ku and J. R. Hwu, Heterocycles, 1993, 36, 323 CAS.
  41. M.-J. Shiao, L.-L. Lai, W.-S. Ku, P.-Y. Lin and J. R. Hwu, J. Org. Chem., 1993, 58, 4742 CrossRef CAS.
  42. R. G. Vogt, in Pheromone Biochemistry, ed. G. D. Prestwich and G. J. Blomquist, Academic Press, New York, 1987 Search PubMed.
  43. J. Rokach and J. Adams, Acc. Chem. Res., 1985, 18, 87 CrossRef CAS.
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