DOI QR코드

DOI QR Code

DFT Calculation on the Stereochemistry of the Allylic Oxidation. Selenium Dioxide-Mediated Oxidation of an Exocyclic Olefinic Hydrindane Compound

  • Ra, Choon-Sup (Department of Chemistry and Institute of Natural Science, Yeungnam University) ;
  • Park, Eun-Mook (Department of Chemistry and Institute of Natural Science, Yeungnam University) ;
  • Park, Gyoo-Soon (Department of Chemistry, Kookmin University)
  • Published : 2008.12.20

Abstract

Keywords

References

  1. Bulman Page, P. C.; McCarthy, T. J. In Comprehensive 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. Fairlamb, I. J. S.; Dickinson, J. M.; Pegg, M. Tetrahedron Lett. 2001, 42, 2205 https://doi.org/10.1016/S0040-4039(01)00110-1
  9. Tauber, A. Y.; Hynninen, P. H. Tetrahedron Lett. 1993, 34, 2979 https://doi.org/10.1016/S0040-4039(00)60498-7
  10. Kshirsagar, T. A.; Moe, S. T.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1704 https://doi.org/10.1021/jo970447z
  11. Madec, D.; Ferezou, J. P. Synlett 1996, 867
  12. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404 https://doi.org/10.1021/jo00157a002
  13. de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809 https://doi.org/10.1021/ja026872d
  14. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435 https://doi.org/10.1021/ja00479a027
  15. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404 https://doi.org/10.1021/jo00157a002
  16. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154 https://doi.org/10.1021/ja00775a050
  17. Arigoni, D.; Vasella, A.; Sharpless, K. B.; Jensen, H. P. J. Am. Chem. Soc. 1973, 95, 7917 https://doi.org/10.1021/ja00804a087
  18. Singleton, D. A.; Hang, C. J. Org. Chem. 2000, 65, 7554 https://doi.org/10.1021/jo000922k
  19. Ra, C. S.; Park, G. Tetrahedron Lett. 2003, 44, 1099 https://doi.org/10.1016/S0040-4039(02)02715-6
  20. Frisch, M. J. et al. Gaussian 03, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998
  21. Becke, A. D. J. Chem. Phys. 1993, 98, 5648 https://doi.org/10.1063/1.464913
  22. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785 https://doi.org/10.1103/PhysRevB.37.785

Cited by

  1. Desulfinylation of Prop-2-enesulfinic Acid: Experimental Results and Mechanistic Theoretical Analysis vol.131, pp.27, 2009, https://doi.org/10.1021/ja901565s
  2. Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of natural and unnatural butenolides vol.9, pp.18, 2011, https://doi.org/10.1039/c1ob05709j
  3. Rotation of the Allylselenic Intermediate in Moderating the Stereochemical Course of the Selenium Dioxide-Mediated Allylic Oxidation vol.32, pp.8, 2008, https://doi.org/10.5012/bkcs.2011.32.8.3137
  4. A Bioinspired Catalytic Oxygenase Cascade to Generate Complex Oxindoles vol.126, pp.29, 2008, https://doi.org/10.1002/ange.201403415
  5. A Bioinspired Catalytic Oxygenase Cascade to Generate Complex Oxindoles vol.53, pp.29, 2008, https://doi.org/10.1002/anie.201403415