On the origin of the endo/exo selectivity in Diels–Alder reactions

(Note: The full text of this document is currently only available in the PDF Version )

D. Suárez and J. A. Sordo


Abstract

The endo/exo selectivity in Diels–Alder reactions is analyzed in terms of the pre-reactive van der Waals complexes located on the potential energy surface.


References

  1. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon NY, 1990 CrossRef CAS; K. N. Houk, Y. Li and J. D. Evanseck, Angew. Chem., Int. Ed. Engl., 1992, 31, 682 CrossRef CAS; K. N. Houk, J. González and Y. Li, Acc. Chem. Res., 1995, 28, 81 CrossRef.
  2. K. Alder and G. Stein, Angew. Chem., 1937, 50, 514 CrossRef.
  3. See for example: J. Sauer and R. Sustmann, Angew. Chem., Int. Ed. Engl., 1980, 19, 779 CrossRef CAS; M. F. Ruiz-López, X. Assfeld, J. I. García, J. A. Mayoral and L. Salvatella, J. Am. Chem. Soc., 1993, 115, 8780 CrossRef; D. Suárez, X. Assfeld, J. González, M. F. Ruiz-López, T. L. Sordo and J. A. Sordo, J. Chem. Soc., Chem. Commun., 1994, 1183 Search PubMed; D. Suárez, T. L. Sordo and J. A. Sordo, J. Am. Chem. Soc., 1994, 116, 763 CrossRef; D. Suárez, J. González, T. L. Sordo and J. A. Sordo, J. Org. Chem., 1994, 59, 8058 CrossRef; D. Suárez, R. López, J. Gonzalez, T. L. Sordo and J. A. Sordo, Int. J. Quantum Chem., 1996, 57, 493 CrossRef; M. Sodupe, R. Rios, V. Branchadell, T. Nicholas, A. Oliva and J. J. Dannenberg, J. Am. Chem. Soc., 1997, 119, 4232 CrossRef and references cited therein.
  4. J. Cioslowski, J. Sauer, J. Hetzenegger, T. Karacher and J. Hierstetter, J. Am. Chem. Soc., 1993, 115, 1353 CrossRef CAS.
  5. (a) J. Z. Gillies, C. W. Gillies, R. D. Suenram, F. J. Lovas and W. Stahal, J. Am. Chem. Soc., 1991, 113, 2421 Search PubMed; (b) C. W. Gillies, J. Z. Gillies, R. D. Suenram, F. J. Lovas, E. Kraka and D. Cramer, J. Am. Chem. Soc., 1991, 113, 2412 CrossRef CAS; (c) K. R. Leopold, G. T. Fraser, S. E. Novick and W. Klemperer, Chem. Rev., 1994, 94, 1807 CrossRef CAS.
  6. S. L. Craig and A. J. Stone, J. Chem. Soc., Faraday Trans., 1994, 90, 1663 RSC.
  7. (a) For major reviews, see V. D. Kiselev and A. I. Konovalov, Russ. Chem. Rev., 1989, 58, 230 CrossRef; C. Cativiela, J. I. García, J. A. Mayoral and L. Salvatella, Chem. Soc. Rev., 1996, 25, 209 Search PubMed; (b) R. López, M. F. Ruiz-López, D. Rinaldi, J. A. Sordo and T. L. Sordo, J. Phys. Chem., 1996, 100, 10 600 Search PubMed; (c) K. B. Wiberg, T. A. Keith, M. J. Frisch and M. Murcko, J. Phys. Chem., 1995, 99, 9072 CrossRef CAS; (d) R. D. Bach, J. E. Winter and J. J. W. McDovall, J. Am. Chem. Soc., 1995, 117, 8586 CrossRef CAS.
  8. L. M. Stephenson, D. E. Smith and S. P. Current, J. Org. Chem., 1982, 47, 4170 CrossRef CAS.
  9. S. F. Boys and F. Bernardi, Mol. Phys., 1970, 19, 553 CrossRef CAS.
  10. S. S. Xantheas, J. Chem. Phys., 1996, 104, 8821 CrossRef CAS.
  11. J. A. Sordo, J. Chem. Phys., 1997, 106, 6204 CrossRef CAS; V. M. Rayón and J. A. Sordo, J. Phys. Chem., 1997, 101, 7414 Search PubMed; V. M. Rayón and J. A. Sordo, J. Chem. Phys., 1997, 107, 7912 CrossRef; V. M. Rayón and J. A. Sordo, Theor. Chem. Acc., in the press Search PubMed.
  12. D. Y. Curtin, Rec. Chem. Progr., 1954, 15, 111 Search PubMed ; For an excellent review, see J. I. Seeman, Chem. Rev., 1983, 83, 83 CrossRef CAS.
  13. See for example: M. I. Menéndez, J. A. Sordo and T. L. Sordo, J. Phys. Chem., 1992, 96, 1185 CrossRef; R. López, M. I. Menéndez, D. Suárez, T. L. Sordo and J. A. Sordo, Comput. Phys. Commun., 1993, 76, 235 CrossRef; D. Suárez, J. A. Sordo and T. L. Sordo, J. Phys. Chem., 1996, 100, 13 462 Search PubMed.
  14. D. Suárez, T. L. Sordo and J. A. Sordo, J. Org. Chem., 1995, 60, 2848 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.