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Synthesis of (E)-α-Ethynyl-α,β-unsaturated Esters from Allenyl Acetates Catalyzed by DABCO and Their Application to Sonogashira Cross-Coupling Reactions

  • Kim, Hyun-Seok (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Shin, Doo-Sup (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Lee, Kwang-Moo (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Lee, Sang-Kyu (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Kim, Sang-Hyuk (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Lee, Phil-Ho (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University)
  • Published : 2010.03.20

Abstract

Keywords

References

  1. Tsuboi, S.; Kuroda, H.; Takatsuka, S.; Fukawa, T.; Sakai, T.;Utaka, M. J. Org. Chem. 1986, 58, 5952. https://doi.org/10.1021/jo00074a020
  2. Rossi, R.; Bellina,F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54,135. https://doi.org/10.1016/S0040-4020(97)10265-4
  3. Shi, W.; Xiao, F.; Wang, J. J. Org. Chem. 2005, 70, 4318. https://doi.org/10.1021/jo050173c
  4. Wang, Y.; Burton, D. J. Org. Lett. 2006, 8, 5295. https://doi.org/10.1021/ol0620850
  5. Lemay,A. B.; Vulic, K. S.; Ogilvie, W. W. J. Org. Chem. 2006, 71, 3615. https://doi.org/10.1021/jo060144h
  6. Tsukada, N.; Niomiya, S.; Ayoama, Y.; Inoue, Y. Org. Lett.2007, 9, 2919. https://doi.org/10.1021/ol071326g
  7. Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini. P.Tetrahedron 1998, 54, 135. https://doi.org/10.1016/S0040-4020(97)10265-4
  8. Trost, B. M.; Gunzner, J. L.; Yasukata,T. Tetrahedron Lett. 2001, 42, 3775. https://doi.org/10.1016/S0040-4039(01)00596-2
  9. Dai, W.-M.; Wu,A.; Hamaguchi, W. Tetrahedron Lett. 2001, 42, 4211. https://doi.org/10.1016/S0040-4039(01)00707-9
  10. Lemay,A.; Vulic, K.; Ogilivie, W. J. Org. Chem. 2006, 71, 3615. https://doi.org/10.1021/jo060144h
  11. Barma, D. K.; Kundu, A.; Zhang, H.; Mioskowski, C.; Falck, J.R. J. Am. Chem. Soc. 2003, 125, 3218. https://doi.org/10.1021/ja029938d
  12. Forti, L.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron Lett. 1995,36, 3023. https://doi.org/10.1016/0040-4039(95)00416-A
  13. Kim, K. M.; Park, I. H. Synthesis 2004, 2641.
  14. Kruper, W. J., Jr.; Emmons, A. H. J. Org. Chem. 1991, 56, 3323. https://doi.org/10.1021/jo00010a027
  15. Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1995,36, 3687. https://doi.org/10.1016/0040-4039(95)00612-G
  16. Buschmann, E.; Schafer, B. Tetrahedron 1994, 50, 2433. https://doi.org/10.1016/S0040-4020(01)86960-X
  17. Satoh, T.; Itoh, N.; Onda, K.; Kitoh, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 2800. https://doi.org/10.1246/bcsj.65.2800
  18. Ishihara, T.; Shintani, A.;Yamanaka, H. Tetrahedron Lett. 1998, 39, 4865. https://doi.org/10.1016/S0040-4039(98)00949-6
  19. Villieras, J.; Perriot, P.; Normant, J. F. Synthesis 1978, 1, 31.
  20. Chan, T. H.; Moreland, M. Tetrahedron Lett. 1978, 6, 515.
  21. Karrenbrock, F.; Schaefer, H. J. Tetrahedron Lett. 1979, 31, 2913.
  22. Zapata, A.; Ferrer, G. F. Synth. Commun. 1986, 16, 1611. https://doi.org/10.1080/00397918608056417
  23. Huang, Z.-Z.; Wu, L.-L.; Zhu, L.-S.; Huang, X. Synth. Commun. 1996, 26, 677. https://doi.org/10.1080/00397919608086740
  24. Braun, N. A.; Buerkle, U.; Feth, M. P.; Klein, I.;Spitzner, D. Eur. J. Org. Chem. 1998, 8, 1569.
  25. Sano, S.; Ando,T.; Yokoyama, K.; Nagao, Y. Synlett 1998, 777.
  26. Tago, K.;Kogen, H. Tetrahedron Lett. 2000, 56, 8825. https://doi.org/10.1016/S0040-4020(00)00811-5
  27. Denney, D. B.; Ross, S. T. J. Org. Chem. 1962, 27, 998. https://doi.org/10.1021/jo01050a075
  28. Yasui, S.; Nakamura, K.; Fujii, M.; Ohno, A. J. Org. Chem. 1985,50, 3283. https://doi.org/10.1021/jo00218a008
  29. Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R.Tetrahedron Lett. 1994, 35, 6913. https://doi.org/10.1016/0040-4039(94)85040-2
  30. Rousseau, G.; Marie, J.-X.Synth. Commun. 1999, 29, 3705. https://doi.org/10.1080/00397919908086009
  31. Zhang, X.; Qing, F.-L.; Yang,Y.; Yu, J.; Fu, X.-K. Tetrahedron Lett. 2000, 41, 2953. https://doi.org/10.1016/S0040-4039(00)00279-3
  32. Tago,K.; Kogen, H. Org. Lett. 2000, 2, 1975. https://doi.org/10.1021/ol006074x
  33. Zhang, X.; Qing, F.-L.;Yu, Y. J. Org. Chem. 2000, 65, 7075. https://doi.org/10.1021/jo005520r
  34. Hamelin, J.; Saoudi, A.;Benhaoua, H. Synthesis 2003, 2185.
  35. Chang, M. Y.; Sun, P. P.;Chen, S. T.; Chang, N. C. Tetrahedron Lett. 2003, 44, 5271. https://doi.org/10.1016/S0040-4039(03)01278-4
  36. Olpp, T.; Bruckner, R. Synthesis 2004, 2135.
  37. Sakamoto, R.;Murata, M.; Nishihara, H. Angew. Chem. Int. Ed. 2006, 45, 4793. https://doi.org/10.1002/anie.200601067
  38. Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem. Int. Ed. 2002,41, 3901. https://doi.org/10.1002/1521-3773(20021018)41:20<3901::AID-ANIE3901>3.0.CO;2-S
  39. Lee, P. H.; Lee, K. Angew. Chem. Int. Ed. 2005, 44,3253. https://doi.org/10.1002/anie.200461957
  40. Lee, P. H.; Lee, K.; Kang, Y. J. Am. Chem. Soc. 2006,128, 1139. https://doi.org/10.1021/ja054144v
  41. Kim, H.; Livinghouse, T.; Seomoon, D.; Lee, P.H. Bull. Korean Chem. Soc. 2007, 28, 1127. https://doi.org/10.5012/bkcs.2007.28.7.1127
  42. Kim, S.; Lee, K.;Seomoon, D.; Lee, P. H. Adv. Synth. Catal. 2007, 349, 2449. https://doi.org/10.1002/adsc.200700309
  43. Yu, H.; Lee, P. H. J. Org. Chem. 2008, 73, 5183. https://doi.org/10.1021/jo800594y
  44. Lee, K.; Lee,P. H. Org. Lett. 2008, 10, 2441. https://doi.org/10.1021/ol800719g
  45. Kim, S.; Lee, P. H. Eur. J. Org. Chem. 2008, 2262.
  46. Kim, S.; Lee, P. H. Adv. Synth. Catal. 2008,350, 547. https://doi.org/10.1002/adsc.200700471
  47. Lee, K.; Lee, P. H. Bull. Korean Chem. Soc. 2008,29, 487. https://doi.org/10.5012/bkcs.2008.29.2.487
  48. Park, C.; Lee, P. H. Org. Lett. 2008, 10, 3359. https://doi.org/10.1021/ol801196g
  49. Choi, Y.; Lee, P. H. Org. Lett. 2009, 11, 1445. https://doi.org/10.1021/ol9001703

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