Bulletin of the Korean Chemical Society

  • 제28권11호
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  • Pages.2051-2055
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  • 2007
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Solvent Effect on Sulfur Ylide Mediated Epoxidation Reaction

  • Lee, Hee-Yoon (Center for Molecular Design and Synthesis, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology) ;
  • Bae, Im-Hyuck (Center for Molecular Design and Synthesis, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology) ;
  • Min, Kyung-Hyun (Center for Molecular Design and Synthesis, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology)
  • 발행 : 2007.11.20
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초록

The solvent effect on sulfur ylide mediated epoxidation reaction was studied systematically. While higher trans/cis ratio of the epoxide was obtained in the more polar solvent, protic solvent produced the lower trans/ cis ratio than any aprotic solvent.

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참고문헌

  1. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.; VCH: New York, 2000; pp 231-280
  2. Katsuki, T. In Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.; VCH: New York, 2000; pp 287-325
  3. Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; pp 649-677
  4. Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J. R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11225
  5. Tosen, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 409
  6. Arai, S.; Tokumaru, K.; Aoyama, T. Tetrahedron Lett. 2004, 45, 1845 https://doi.org/10.1016/j.tetlet.2004.01.009
  7. Aggarwal, V. K.; Hynd, G.; Picoul, W.; Vasse, J.-L. J. Am. Chem. Soc. 2002, 124, 9964
  8. Johnson, A. W.; LaCount, R. B. J. Am. Chem. Soc. 1961, 83, 417 https://doi.org/10.1021/ja01463a040
  9. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353 https://doi.org/10.1021/ja01084a034
  10. Aggarwal, V. K. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; pp 679-693
  11. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341
  12. Furukawa, N.; Sugihara, Y.; Fujihara, H. J. Org. Chem. 1989, 54, 4222 https://doi.org/10.1021/jo00278a045
  13. Julienne, K.; Metzner, P. J. Org. Chem. 1998, 63, 4532 https://doi.org/10.1021/jo980269p
  14. Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.; Metzner, P. J. Org. Chem. 2001, 66, 5620 https://doi.org/10.1021/jo015588m
  15. Zanardi, J.; Lamazure, D.; Miniere, S.; Reboul, V.; Metzner, P. J. Org. Chem. 2002, 67, 9083 https://doi.org/10.1021/jo026085z
  16. Solladie-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494
  17. Diep-Vohuule, A.; Solladie-Cavallo, A. Tetrahedron: Asymm. 1996, 7, 1783
  18. Solladie-Cavallo, A.; Bouerat, L.; Roje, M. Tetrahedron Lett. 2000, 41, 7309
  19. Solladie-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077
  20. Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489
  21. Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. J. Chem. Soc., Perkin Trans. 1 1999, 77
  22. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem. Int. Ed. 2001, 40, 1430 https://doi.org/10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO;2-W
  23. Aggarwal, V. K.; Angelaud, R.; Bihan, D.; Blackburn, P.; Fieldhouse, R.; Fonquerna, S. J.; Ford, G. D.; Hynd, G.; Jones, E.; Jones, R. V. H.; Jubault, P.; Palmer, M. J.; Ratcliffe, R. D.; Adams, H. J. Chem. Soc., Perkin Trans. 1 2001, 2604
  24. Aggarwal, V. K.; Bae, I.; Lee, H.-Y.; Richardson, J.; Williams, D. T. Angew. Chem. Int. Ed. 2003, 42, 3274 https://doi.org/10.1002/anie.200350968
  25. Aggarwal, V. K.; Richardson, J. Chem. Commun. 2003, 2644
  26. Aggarwal, V. K.; Calamai, S.; Ford, J. G. J. Chem. Soc., Perkin Trans. 1 1997, 593
  27. Aggarwal, V. K.; Ford, J. G.; Fonquerna, S.; Adams, H.; Jones, R. V. H.; fieldhouse, R. J. Am. Chem. Soc. 1998, 120, 8328 https://doi.org/10.1021/ja9812150
  28. Lindvall, M. K.; Koskinen, A. M. P. J. Org. Chem. 1999, 64, 4596 https://doi.org/10.1021/jo9818935
  29. Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747 https://doi.org/10.1021/ja025633n
  30. Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926 https://doi.org/10.1021/ja034606+
  31. Julienne, K.; Metzner, P.; Henryon, V. J. Chem. Soc., Perkin Trans. 1 1999, 731
  32. Saito, T.; Akiba, D.; Sakairi, M.; Kanazawa, S. Tetrahedron Lett. 2001, 42, 57 https://doi.org/10.1016/S0040-4039(00)01878-5
  33. Saito, T.; Akiba, D.; Sakairi, M.; Ishikawa, K.; Otani, T. ARKIVOC 2004, ii, 152
  34. Zhou, Y.-G.; Li, A.-H.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1996, 1353
  35. Aggarwal, V. K.; Abdel-Rahman, H.; Jones, R. V. H.; Lee, H.-Y.; Reid, B. D. J. Am. Chem. Soc. 1994, 116, 5973
  36. Aggarwal, V. K.; Abdel-Rahman, H.; Fan, L.; Jones, R. V. H.; Standen, M. C. H. Chem. Eur. J. 1996, 2, 1024
  37. Snyder, J. P. Tetrahedron Lett. 1971, 215
  38. Bergelson, L. D.; Barsukov, L. I.; Shmyakin, M. M. Tetrahedron 1967, 23, 2709 https://doi.org/10.1016/0040-4020(67)85136-6
  39. Wang, Q.; Khoury, M. E.; Schlosser, M. Chem. Eur. J. 2000, 6, 420 https://doi.org/10.1002/(SICI)1521-3765(20000204)6:3<420::AID-CHEM420>3.0.CO;2-H

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