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One-Pot Synthesis of Esters through a Benzoin Condensation-Oxidative Cleavage-Esterification Triple Cascade Reaction

  • Kim, Mi-Jin (Department of Chemistry, Sungkyunkwan University) ;
  • Yang, Jung-Woon (Department of Energy Science, Sungkyunkwan University)
  • 투고 : 2012.06.09
  • 심사 : 2012.06.16
  • 발행 : 2012.09.20

초록

키워드

참고문헌

  1. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167. https://doi.org/10.1038/nchem.539
  2. Alba, A.-N. R.; Companyo, X.; Viciano, M.; Rios, R. Curr. Org. Chem. 2009, 13, 1432. https://doi.org/10.2174/138527209789055054
  3. Moyano, A.; Rios, R. Chem. Rev. 2011, 111, 4703. https://doi.org/10.1021/cr100348t
  4. Enders, D.; Breuer, K. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999, 1093.
  5. 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.
  6. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 42, 55.
  7. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534. https://doi.org/10.1021/ar030050j
  8. Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2988. https://doi.org/10.1002/anie.200603380
  9. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606. https://doi.org/10.1021/cr068372z
  10. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691. https://doi.org/10.1039/b719083m
  11. Christmann, M. Angew. Chem. Int. Ed. 2005, 44, 2632. https://doi.org/10.1002/anie.200500761
  12. Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126. https://doi.org/10.1021/ja047407e
  13. Reynolds, N. T.; Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518. https://doi.org/10.1021/ja046991o
  14. Chan, A.; Scheidt, K. Org. Lett. 2005, 7, 905. https://doi.org/10.1021/ol050100f
  15. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873. https://doi.org/10.1021/ol051269w
  16. Reynolds, N. T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406. https://doi.org/10.1021/ja055918a
  17. Phillips, E. M.; Wadamoto, M.; Chan, A.; Scheidt, K. A. Angew. Chem. Int. Ed. 2007, 46, 3107. https://doi.org/10.1002/anie.200605235
  18. Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. Tetrahedron 2009, 65, 3102. https://doi.org/10.1016/j.tet.2008.10.033
  19. Rosa, J. N.; Reddy, R. S.; Candeias, N. R.; Cal, P. M. S. D.; Gois, P. M. P. Org. Lett. 2010, 12, 2686. https://doi.org/10.1021/ol100302e
  20. Guin, J.; De Sarkar, S.; Grimme, S.; Studer, A. Angew. Chem. Int. Ed. 2008, 47, 8727. https://doi.org/10.1002/anie.200802735
  21. Maji, B.; Vedachalan, S.; Ge, X.; Cai, S.; Liu, X.- W. J. Org. Chem. 2011, 76, 3016. https://doi.org/10.1021/jo200275c
  22. Lin, L.; Li, Y.; Du, W.; Deng, W.-P. Tetrahedron Lett. 2010, 51, 3571. https://doi.org/10.1016/j.tetlet.2010.05.003
  23. Xin, Y.-C.; Shi, S.-H.; Xie, D.-D.; Hui, X.-P.; Xu, P.-F. Eur. J. Org. Chem. 2011, 6527.
  24. Wang, X.; Wang, D. Z. Tetrahedron 2011, 67, 3406. https://doi.org/10.1016/j.tet.2011.03.052
  25. Kang, S.; Joo, C.; Kim, S. M.; Han, H.; Yang, J. W. Tetrahedron Lett. 2011, 52, 502. https://doi.org/10.1016/j.tetlet.2010.11.079
  26. Kim, S. M.; Kim, Y. S.; Yang, J. W. Bull. Korean Chem. Soc. 2011, 32, 2529. https://doi.org/10.5012/bkcs.2011.32.8.2529
  27. Hesek, D.; Lee, M.; Noll, B. C.; Fisher, J. F.; Mobashery, S. J. Org. Chem. 2009, 74, 2567. https://doi.org/10.1021/jo802706d
  28. Werner, T.; Koch, J. Eur. J. Org. Chem. 2010, 6904.
  29. Xu, L-W.; Gao, Y.; Yin, J.- J.; Li, L.; Xia, C.-G. Tetrahedron Lett. 2005, 46, 5317. https://doi.org/10.1016/j.tetlet.2005.06.015
  30. Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. https://doi.org/10.1021/jo00354a030
  31. Sarkar, S. D.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190. https://doi.org/10.1021/ja910540j
  32. Xiang, J.; Orita, A.; Otera, J. Angew. Chem. Int. Ed. 2002, 41, 4117. https://doi.org/10.1002/1521-3773(20021104)41:21<4117::AID-ANIE4117>3.0.CO;2-4
  33. Iranpoor, N.; Firouzabadi, H.; Khalili, D. Org. Biomol. Chem. 2010, 8, 4436. https://doi.org/10.1039/c004357e
  34. Held, I.; Hoff, P. von den.; Stephenson, D. S.; Zipse, H. Adv. Synth. Catal. 2008, 350, 1891. https://doi.org/10.1002/adsc.200800268
  35. Ren, W.; Emi, A.; Yamane, M. Synthesis 2001, 14, 2302.
  36. Katritzky, A. R.; Denisko, O. V.; Fang, Y.; Zhang, L.; Wang, Z. ARKIVOC 2001, XI, 41.
  37. Ishihara, K.; Niwa, M.; Kosugi, Y. Org. Lett. 2008, 10, 2187. https://doi.org/10.1021/ol8005979
  38. Yamamoto, Y. Adv. Synth. Catal. 2010, 352, 478. https://doi.org/10.1002/adsc.200900836

피인용 문헌

  1. An asymmetric normal-electron-demand aza-Diels–Alder reaction via trienamine catalysis vol.11, pp.47, 2013, https://doi.org/10.1039/c3ob41698d
  2. Metal-Free Aerobic Oxidative Esterification of Aldehydes in the Presence of Cyanide vol.36, pp.8, 2015, https://doi.org/10.1002/bkcs.10398