Bulletin of the Korean Chemical Society

  • 제32권3호
  • /
  • Pages.1087-1090
  • /
  • 2011
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Remarkable Rate Acceleration of Baylis-Hillman Reaction of Notorious α,β-Unsaturated Aldehydes Catalyzed by Proton Donor

  • Kim, Ko-Hoon (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Hyun-Seung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Yu-Mi (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • 투고 : 2011.01.08
  • 심사 : 2011.01.18
  • 발행 : 2011.03.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

키워드

참고문헌

  1. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891. https://doi.org/10.1021/cr010043d
  2. Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769-8780. https://doi.org/10.1016/j.tet.2009.07.034
  3. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645. https://doi.org/10.2174/1385272023374094
  4. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490. https://doi.org/10.5012/bkcs.2005.26.10.1481
  5. Radha Krishna, P.; Sachwani, R.; Reddy, P. S. Synlett 2008, 2897-2912.
  6. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1-48. https://doi.org/10.1021/cr068057c
  7. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574. https://doi.org/10.1016/j.tet.2008.02.087
  8. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447-5674 and further references cited therein. https://doi.org/10.1021/cr900291g
  9. Song, Y.; Ke, H.; Wang, N.; Wang, L.; Zou, G. Tetrahedron 2009, 65, 9086-9090. https://doi.org/10.1016/j.tet.2009.09.049
  10. Hsu, J.-C.; Yen, Y.-H.; Chu, Y.-H. Tetrahedron Lett. 2004, 45, 4673-4676. https://doi.org/10.1016/j.tetlet.2004.04.099
  11. Jeong, Y.; Ryu, J.-S. J. Org. Chem. 2010, 75, 4183-4191. https://doi.org/10.1021/jo100618d
  12. Johnson, C. L.; Donkor, R. E.; Nawaz, W.; Karodia, N. Tetrahedron Lett. 2004, 45, 7359-7361. https://doi.org/10.1016/j.tetlet.2004.07.155
  13. Rosa, J. N.; Afonso, C. A. M.; Santos, A. G. Tetrahedron 2001, 57, 4189-4193. https://doi.org/10.1016/S0040-4020(01)00316-7
  14. Chandrasekhar, S.; Narsihmulu, C.; Sartitha, B.; Sultana, S. S. Tetrahedron Lett. 2004, 45, 5865-5867. https://doi.org/10.1016/j.tetlet.2004.05.153
  15. Cho, J.-H.; Ko, S. Y.; Oh, E.; Park, J. C.; Yoo, J. U. Helv. Chim. Acta 2002, 85, 3994-3999. https://doi.org/10.1002/1522-2675(200211)85:11<3994::AID-HLCA3994>3.0.CO;2-2
  16. Lee, W.-D.; Yang, K.-S.; Chen, K. Chem. Commun. 2001, 1612-1613.
  17. Nakano, A.; Kawahara, S.; Akamatsu, S.; Morokuma, K.; Nakatani, M.; Iwabuchi, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Tetrahedron 2006, 62, 381-389. https://doi.org/10.1016/j.tet.2005.09.072
  18. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220. https://doi.org/10.1021/ja992655+
  19. Leadbeater, N. E.; van der Pol, C. J. Chem. Soc., Perkin Trans. 1 2001, 2831-2835.
  20. Kawamura, M.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 1539-1542. https://doi.org/10.1016/S0040-4039(98)02705-1
  21. Bhuniya, D.; Narayanan, S.; Lamba, T. S.; Krishna Reddy, K. V. S. R. Synth. Commun. 2003, 33, 3717-3726. https://doi.org/10.1081/SCC-120025180
  22. Maher, D. J.; Connon, S. J. Tetrahedron Lett. 2004, 45, 1301-1305. https://doi.org/10.1016/j.tetlet.2003.11.062
  23. Shi, M.; Liu, X.-G. Org. Lett. 2008, 10, 1043-1046. https://doi.org/10.1021/ol7028806
  24. Amarante, G. W.; Benassi, M.; Milagre, H. M. S.; Braga, A. A. C.; Maseras, F.; Eberlin, M. N.; Coelho, F. Chem. Eur. J. 2009, 15, 12460-12469. https://doi.org/10.1002/chem.200900966
  25. Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003, 68, 692-700. https://doi.org/10.1021/jo026671s
  26. Aggarwal, V. K.; Dean, D. K.; Mereu, A.; Williams, R. J. Org. Chem. 2002, 67, 510-514. https://doi.org/10.1021/jo016073y
  27. Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413-5418. https://doi.org/10.1021/jo015628m
  28. de Souza, R. O. M. A.; Pereira, V. L. P.; Esteves, P. M.; Vasconcellos, M. L. A. A. Tetrahedron Lett. 2008, 49, 5902-5905. https://doi.org/10.1016/j.tetlet.2008.07.140
  29. Gruttadauria, M.; Giacalone, F.; Meo, P. L.; Marculescu, A. M.; Riela, S.; Noto, R. Eur. J. Org. Chem. 2008, 1589-1596.
  30. Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183-7189. https://doi.org/10.1021/jo980421n
  31. Yang, K.-S.; Lee, W.-D.; Pan, J.-F.; Chen, K. J. Org. Chem. 2003, 68, 915-919. https://doi.org/10.1021/jo026318m
  32. Yukawa, T.; Seelig, B.; Xu, Y.; Morimoto, H.; Matsunaga, S.; Berkessel, A.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 11988-11992. https://doi.org/10.1021/ja103294a
  33. Shi, M.; Liu, Y.-H. Org. Biomol. Chem. 2006, 1468-1470.
  34. Shi, M.; Chen, L.-H.; Li, C.-Q. J. Am. Chem. Soc. 2005, 127, 3790-3800. https://doi.org/10.1021/ja0447255
  35. Liu, Y.-h.; Shi, M. Adv. Synth. Catal. 2008, 350, 122-128. https://doi.org/10.1002/adsc.200700338
  36. Yamada, Y. M. A.; Ikegami, S. Tetrahedron Lett. 2000, 41, 2165-2169. https://doi.org/10.1016/S0040-4039(00)00125-8
  37. Zhong, W.; Zheng, Y.; Zhou, J.; Shen, Y. Synlett 2010, 3057-3060.
  38. Garnier, J.-M.; Anstiss, C.; Liu, F. Adv. Synth. Catal. 2009, 351, 331-338. https://doi.org/10.1002/adsc.200800679
  39. McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094-12095. https://doi.org/10.1021/ja037705w
  40. McDougal, N. T.; Trevellini, W. L.; Rodgen, S. A.; Kliman, L. T.; Schaus, S. E. Adv. Synth. Catal. 2004, 346, 1231-1240. https://doi.org/10.1002/adsc.200404122
  41. Narender, P.; Gangadasu, B.; Ravinder, M.; Srinivas, U.; Swamy, G. Y. S. K.; Ravikumar, K.; Rao, V. J. Tetrahedron 2006, 62, 954-959. https://doi.org/10.1016/j.tet.2005.10.032
  42. Grainger, R. S.; Leadbeater, N. E.; Pamies, A. M. Catal. Commun. 2002, 3, 449- 452. https://doi.org/10.1016/S1566-7367(02)00178-4
  43. Abermil, N.; Masson, G.; Zhu, J. Org. Lett. 2009, 11, 4648-4651. https://doi.org/10.1021/ol901920s
  44. Abermil, N.; Masson, G.; Zhu, J. J. Am. Chem. Soc. 2008, 130, 12596-12597. https://doi.org/10.1021/ja805122j
  45. Cai, J.; Zhou, Z.; Zhao, G.; Tang, C. Org. Lett. 2002, 4, 4723-4725. https://doi.org/10.1021/ol027197f

피인용 문헌

  1. ChemInform Abstract: Remarkable Rate Acceleration of Baylis-Hillman Reaction of Notorious α,β-Unsaturated Aldehydes Catalyzed by Proton Donor. vol.42, pp.28, 2011, https://doi.org/10.1002/chin.201128064
  2. Synthesis of 1,3,4-Trisubstituted Benzenes from Morita-Baylis-Hillman Adducts of α-Bromocinnamaldehyde via [5+1] Annulation Strategy vol.36, pp.12, 2015, https://doi.org/10.1002/bkcs.10577
  3. A Practical Synthesis of Morita-Baylis-Hillman Adducts of Aryl Vinyl Ketones Catalyzed by a Proton Donor vol.33, pp.6, 2011, https://doi.org/10.5012/bkcs.2012.33.6.2023
  4. Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives vol.10, pp.None, 2011, https://doi.org/10.3762/bjoc.10.315
  5. Chemoselective and Highly Rate Accelerated Intramolecular Aza-Morita-Baylis-Hillman Reaction vol.83, pp.23, 2018, https://doi.org/10.1021/acs.joc.8b02310