Bulletin of the Korean Chemical Society

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Rotation of the Allylselenic Intermediate in Moderating the Stereochemical Course of the Selenium Dioxide-Mediated Allylic Oxidation

  • Received : 2011.03.04
  • Accepted : 2011.03.18
  • Published : 2011.08.20
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Abstract

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References

  1. Bulman P.; McCarthy, T. J. In Compre- hensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 83.
  2. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
  3. Wilkinson, S. G. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 1, p 579.
  4. Rabjohn, N. Org. React. 1978, 24, 261.
  5. Campbell, T. W.; Walker, H. G.; Coppinger, G. M. Chem. Rev. 1952, 50, 279. https://doi.org/10.1021/cr60156a003
  6. Rabjohn, N. Org. React. 1949, 5, 331.
  7. Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235. https://doi.org/10.1021/cr60115a001
  8. Muzart, J. Chem. Rev. 1992, 92, 113. https://doi.org/10.1021/cr00009a005
  9. Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205. https://doi.org/10.1016/S0040-4039(01)00110-1
  10. Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704. https://doi.org/10.1021/jo970447z
  11. Li, Y.; Wu, X.; Lee, T. B.; Isbell, E. K.; Parish, E. J.; Gorden, E. V. J. Org. Chem. 2010, 75, 1807 https://doi.org/10.1021/jo902637k
  12. Zhao. Y.; Yeung, Y-.Y. Org. Lett. 2010, 12, 2128. https://doi.org/10.1021/ol100603q
  13. Salvador, J. A. R.; Clark, J. H. Chem. Commun. 2001, 6, 33.
  14. Jurado- Gonzalez, M.; Sullivan, A. C.; Wilson, J. R. H. Tetrahedron Lett. 2003, 44, 4283. https://doi.org/10.1016/S0040-4039(03)00833-5
  15. Yu, J. Q.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 3232. https://doi.org/10.1021/ja0340735
  16. Yu, J. Q.; Wu, H. C.; Corey, E. J. Org. Lett. 2005, 7, 1415. https://doi.org/10.1021/ol050284y
  17. Catino, A. J.; Forslund, R. E.; Doyle, M. P. J. Am. Chem. Soc. 2004, 126, 13622. https://doi.org/10.1021/ja045330o
  18. Catino, A. J.; Nichols, J. M.; Choi, H.; Gottipamula, S.; Doyle, M. P. Org. Lett. 2005, 7, 5167. https://doi.org/10.1021/ol0520020
  19. Choi, H.; Doyle, M. P. Org. Lett. 2007, 9, 5349. https://doi.org/10.1021/ol7025284
  20. McLaughlin, E. C.; Choi, H.; Wang, K.; Chiou, G.; Doyle, M. P. J. Org. Chem. 2009, 74, 730. https://doi.org/10.1021/jo8021132
  21. McLaughlin, E. C.; Doyle, M. P. J. Org. Chem. 2008, 73, 4317. https://doi.org/10.1021/jo800382p
  22. Shing, T. K. M.; Yeung, Y.-Y.; Su, P. L. Org. Lett. 2006, 8, 3149. https://doi.org/10.1021/ol0612298
  23. Silvestre, S. M.; Salvador, J. A. R. Tetrahedron 2007, 63, 2439. https://doi.org/10.1016/j.tet.2007.01.012
  24. Salvador, J. A. R.; Silvestre, S. M. Tetrahedron Lett. 2005, 46, 2581. https://doi.org/10.1016/j.tetlet.2005.02.080
  25. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154. https://doi.org/10.1021/ja00775a050
  26. Arigoni, D.; Vasella, A.; Sharpless, K. B.; Jensen, H. P. J. Am. Chem. Soc. 1973, 95, 7917. https://doi.org/10.1021/ja00804a087
  27. Bhalerao, U. T.; Rapoport, H. J. Am. Chem. Soc. 1971, 93, 4835. https://doi.org/10.1021/ja00748a028
  28. Singleton, D. A.; Hang, C. J. Org. Chem. 2000, 65, 7554. https://doi.org/10.1021/jo000922k
  29. Ra, C. S.; Park, G. Tetrahedron Lett. 2003, 44, 1099. https://doi.org/10.1016/S0040-4039(02)02715-6
  30. Park, G.; Hwang, J.-C.; Jung, W. S.; Ra, C. S. Bull. Korean Chem. Soc. 2005, 26, 1856. https://doi.org/10.5012/bkcs.2005.26.11.1856
  31. Ra, C. S.; Park, E. M.; Park, G. Bull. Korean Chem. Soc. 2008, 29, 2513. https://doi.org/10.5012/bkcs.2008.29.12.2513
  32. Frisch, M. J.; et al. Gaussian 98, Revision A.11.3, Gaussian, Inc., Pittsburgh, PA, 2002.
  33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. https://doi.org/10.1063/1.464913
  34. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. https://doi.org/10.1103/PhysRevB.37.785
  35. de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809. https://doi.org/10.1021/ja026872d
  36. Ogliaro, F.; Harris, N.; Cohen, S.; Filatov, M.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 8977. https://doi.org/10.1021/ja991878x
  37. de Visser, S. P.; Ogliaro, F.; Harris, N.; Shaik, S. J. Am. Chem. Soc. 2001, 123, 3037. https://doi.org/10.1021/ja003544+
  38. Groves, J. T.; Han, Y.-Z. In Cytochrome P450: Structures, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; Chapter 1.
  39. Ogliaro, F.; Cohen, S.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 12892. https://doi.org/10.1021/ja005619f
  40. Ogliaro, F.; de Visser, S. P.; Groves, J. T.; Shaik, S. Angew. Chem., Int. Ed. 2001, 40, 2874. https://doi.org/10.1002/1521-3773(20010803)40:15<2874::AID-ANIE2874>3.0.CO;2-9
  41. Bernadou, J.; Fabiano, A.-S.; Robert, A.; Meunier, B. J. Am. Chem. Soc. 1994, 116, 9375. https://doi.org/10.1021/ja00099a083

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