Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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An Efficient Synthesis of α,α-Diallyl Carbinols from Esters Activated with Amides via an In-Mediated Barbier Type Allylation

  • Kim, Yu-Mi (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Sung-Hwan (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)
  • Received : 2010.03.27
  • Accepted : 2010.04.14
  • Published : 2010.06.20
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References

  1. Auge, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739-1764.
  2. Kargbo, R. B.; Cook, G. R. Curr. Org. Chem. 2007, 11, 1287-1309. https://doi.org/10.2174/138527207782023139
  3. Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 17-28. https://doi.org/10.5012/bkcs.2007.28.1.017
  4. Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149-11176. https://doi.org/10.1016/S0040-4020(99)00641-9
  5. Pae, A. N.; Cho, Y. S. Curr. Org. Chem. 2002, 6, 715-737. https://doi.org/10.2174/1385272023374030
  6. Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959-1982. https://doi.org/10.1016/j.tet.2003.12.037
  7. Podlech, J.; Maier, T. C. Synthesis 2003, 633-655.
  8. Fujiwara, N.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 4729-4732. https://doi.org/10.1016/S0040-4039(98)00929-0
  9. Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095-4101. https://doi.org/10.1021/jo990160x
  10. Jin, S.-J.; Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1528-1532. https://doi.org/10.1246/bcsj.66.1528
  11. Ranu, B. C.; Das, A. Tetrahedron Lett. 2004, 45, 6875-6877. https://doi.org/10.1016/j.tetlet.2004.07.098
  12. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 1696-1698. https://doi.org/10.1016/j.tetlet.2009.01.149
  13. Kim, S. H.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2009, 50, 5744-5747. https://doi.org/10.1016/j.tetlet.2009.07.140
  14. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6476-6479. https://doi.org/10.1016/j.tetlet.2009.09.013
  15. Kim, S. H. Kim, S. H.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 860-862. https://doi.org/10.1016/j.tetlet.2009.12.034
  16. Kim, S. H.; Kim, S. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 2774-2777. https://doi.org/10.1016/j.tetlet.2010.03.076
  17. Langer, P.; Schroeder, R. Eur. J. Org. Chem. 2004, 1025-1032.
  18. Chakraborty, K.; Devakumar, C.; Tomar, S. M. S.; Kumar, R. J. Agric. Food Chem. 2003, 51, 992-998. https://doi.org/10.1021/jf025870+
  19. Sellstedt, J. H.; Guinosso, C. J.; Begany, A. J.; Bell, S. C.; Rosenthale, M. J. Med. Chem. 1975, 18, 926-933. https://doi.org/10.1021/jm00243a014
  20. Kuhn, C.; Beckert, R.; Friedrich, M.; Gorls, H. J. Heterocyclic Chem. 2006, 43, 1569-1574. https://doi.org/10.1002/jhet.5570430621
  21. Kitagawa, O.; Momose, S.-i.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett. 1999, 40, 8827-8831. https://doi.org/10.1016/S0040-4039(99)01853-5
  22. Cao, H.; Mundla, S. R.; Cook, J. M. Tetrahedron Lett. 2003, 44, 6165-6168. https://doi.org/10.1016/S0040-4039(03)01418-7
  23. Van Ornum, S. G.; Bruendl, M. M.; Cao, H.; Reddy, M.; Grubisha, D. S.; Bennett, D. W.; Cook, J. M. J. Org. Chem. 2000, 65, 1957-1971. https://doi.org/10.1021/jo9914014
  24. Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry 1997, 8, 3895-3902. https://doi.org/10.1016/S0957-4166(97)00571-5
  25. Van Ornum, S. G.; Cook, J. M. Tetrahedron Lett. 1996, 37, 7185-7188. https://doi.org/10.1016/0040-4039(96)01634-6
  26. Kitagawa, O.; Hanano, T.; Tanabe, K.; Shiro, M.; Taguchi, T. J. Chem. Soc., Chem. Commun. 1992, 1005-1007.
  27. Jia, Y.; Zhang, M.; Tao, F.; Zhou, J. Synth. Commun. 2002, 32, 2829-2835. https://doi.org/10.1081/SCC-120006467
  28. Schmidt, B.; Pohler, M. Org. Biomol. Chem. 2003, 1, 2512-2517. https://doi.org/10.1039/b303441k
  29. Coleman, R. S.; Walczak, M. C.; Campbell, E. L. J. Am. Chem. Soc. 2005, 127, 16038-16039. https://doi.org/10.1021/ja056217g
  30. Bryan, V. J.; Chan, T.-H. Tetrahedron Lett. 1997, 38, 6493-6496. https://doi.org/10.1016/S0040-4039(97)01512-8
  31. Yoo, J.; Oh, K. E.; Keum, G.; Kang, S. B.; Kim, Y. Polyhedron 2000, 19, 549-551. https://doi.org/10.1016/S0277-5387(99)00405-2
  32. Tanaka, H.; Nakahata, S.; Watanabe, H.; Zhao, J.; Kuroboshi, M.; Torii, S. Inorg. Chim. Acta 1999, 296, 204-207. https://doi.org/10.1016/S0020-1693(99)00393-X
  33. Lee, P. H.; Seomoon, D.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1380-1384.
  34. Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721-2724. https://doi.org/10.1016/0040-4039(95)00377-O
  35. Lee, P. H.; Lee, K.; Chang, S. Synth. Commun. 2001, 31, 3189-3196. https://doi.org/10.1081/SCC-100105896
  36. Kaur, P.; Singh, P.; Kumar, S. Tetrahedron 2005, 61, 8231-8240. https://doi.org/10.1016/j.tet.2005.06.045

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