Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Inverse Enantioselectivity with Catalyst Loading in Enantioselective Self-Benzoin Condensation using Triazolium-based N-Heterocyclic Carbene Catalyst

  • Mao, Hui (Department of Energy Science, Sungkyunkwan University) ;
  • An, Shu Lan (Department of Energy Science, Sungkyunkwan University) ;
  • Kim, Sun-Min (Department of Energy Science, Sungkyunkwan University) ;
  • Yang, Jung-Woon (Department of Energy Science, Sungkyunkwan University)
  • Received : 2011.10.04
  • Accepted : 2011.10.08
  • Published : 2011.12.20
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References

  1. List, B.; Yang, J. W. Science 2006, 313, 1584. https://doi.org/10.1126/science.1131945
  2. MacMillan, D. W. C. Nature 2008, 455, 304. https://doi.org/10.1038/nature07367
  3. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726. https://doi.org/10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO;2-D
  4. Jacobsen, E. N.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. 2010, 107, 20618. https://doi.org/10.1073/pnas.1016087107
  5. Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 4638. https://doi.org/10.1002/anie.200704684
  6. Houk, K. N.; List, B. Acc. Chem. Res. 2004, 37, 487. https://doi.org/10.1021/ar040216w
  7. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719. https://doi.org/10.1039/b415217b
  8. Enders, D.; Breuer, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; vol. 3, p 1093.
  9. Enders, D.; Balensiefer, T.; Niemeier, O.; Christmann, M., In Enantioselective Organocatalysis: Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiely-VCH: Weinheim, Germany, 2007; p 331.
  10. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 42, 55.
  11. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534. https://doi.org/10.1021/ar030050j
  12. Zeitler, K. Angew. Chem. Int. Ed. 2005, 44, 7506. https://doi.org/10.1002/anie.200502617
  13. Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2988. https://doi.org/10.1002/anie.200603380
  14. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606. https://doi.org/10.1021/cr068372z
  15. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691. https://doi.org/10.1039/b719083m
  16. Christmann, M. Angew. Chem. Int. Ed. 2005, 44, 2632. https://doi.org/10.1002/anie.200500761
  17. Jones, W. D. J. Am. Chem. Soc. 2009, 131, 15075. https://doi.org/10.1021/ja908253u
  18. Read de Alaniz, J.; Rovis, T. Synlett 2009, 1189.
  19. Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 269.
  20. Sheehan, J. C.; Hunneman, D. H. J. Am. Chem. Soc. 1966, 88, 3666. https://doi.org/10.1021/ja00967a049
  21. Sheehan, J. C.; Hara, T. J. Org. Chem. 1974, 39, 1196. https://doi.org/10.1021/jo00923a006
  22. Knight, R. L.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 1891.
  23. Knight, R. L.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3611. https://doi.org/10.1016/S0040-4039(97)00681-3
  24. Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925. https://doi.org/10.1016/S0040-4039(98)00439-0
  25. Marti, J.; Castells, J.; Lopez-Calahorra, F. Tetrahedron Lett. 1993, 34, 521. https://doi.org/10.1016/0040-4039(93)85117-F
  26. Tachibana, Y.; Kihara, N.; Takata, T. J. Org. Chem. 2004, 126, 3438.
  27. Tagaki, W.; Tamura, Y.; Yano, Y. Bull. Chem. Soc. Jpn. 1980, 53, 478. https://doi.org/10.1246/bcsj.53.478
  28. Gerhard, A. U.; Leeper, F. J. Tetrahedron Lett. 1997, 38, 3615. https://doi.org/10.1016/S0040-4039(97)00682-5
  29. Pesch, J.; Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025.
  30. Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743. https://doi.org/10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO;2-Q
  31. Enders, D.; Han, J. Tetrahedron: Asymmetry 2008, 19, 1367. https://doi.org/10.1016/j.tetasy.2008.05.017
  32. Ma, Y.; Wei, S.; Wu, J.; Yang, F.; Liu, B.; Lan, J.; Yang, S.; You, J. Adv. Synth. Catal. 2008, 350, 2645. https://doi.org/10.1002/adsc.200800371
  33. O'Toole, S. E.; Connon, S. J. Org. Biomol. Chem. 2009, 7, 3584. https://doi.org/10.1039/b908517c
  34. Baragwanath, L.; Rose, C. A.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2009, 74, 9214. https://doi.org/10.1021/jo902018j
  35. Huang, X.; Ye, S. Chin. Sci. Bull. 2010, 55, 1753 https://doi.org/10.1007/s11434-010-3122-7
  36. Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463. https://doi.org/10.1002/anie.200503885
  37. Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 3492. https://doi.org/10.1002/anie.200600268
  38. Enders, D.; Niemeier, O.; Raabe, G. Synlett 2006, 15, 2431.
  39. Li, Y.; Feng, Z.; You, S.- L. Chem. Commun. 2008, 2263.
  40. Jin, M. Y.; Kim, S. M.; Han, H.; Ryu, D. H.; Yang, J. W. Org. Lett. 2011, 13, 880. https://doi.org/10.1021/ol102937w
  41. O'Toole, S. E.; Rose, C. A.; Gundala, S.; Zeitler, K.; Connon, S. J. J. Org. Chem. 2010, 76, 347.
  42. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725. https://doi.org/10.1021/jo050645n
  43. Jang, H. B.; Rho, H. S.; Oh, J. S.; Nam, E. H.; Park, S. E.; Bae, H. Y.; Song, C. E. Org. Biomol. Chem. 2010, 8, 3918. https://doi.org/10.1039/c0ob00047g

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