Bulletin of the Korean Chemical Society

  • 제29권2호
  • /
  • Pages.487-490
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  • 2008
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of Cyclic Compounds Having exo-Methylene Groups through the Diels-Alder Reactions of Vinyl Allenes Obtained from Propargyl Bromide and Indium

  • Lee, Koo-Yeon (Department of Chemistry and Institute for Basic Science, Kangwon National University) ;
  • Lee, Phil-Ho (Department of Chemistry and Institute for Basic Science, Kangwon National University)
  • 발행 : 2008.02.20
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참고문헌

  1. Patai, S., Ed. The Chemistry of Ketenes, Allenes and Related Compounds; Wiley: New York, 1980
  2. The Chemistry of the Allenes; Landor, S. R., Ed.; Academic: London, 1982
  3. Smadja, W. Chem. Rev. 1983, 83, 263 https://doi.org/10.1021/cr00055a003
  4. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984
  5. Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067 https://doi.org/10.1021/cr9902796
  6. Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004
  7. Angelov, C. M.; Mondeshka, D. M.; Tancheva, T. N. Chem. Commun. 1985, 647
  8. Reich, H. J.; Eisenhart, E. K.; Whipple, W. L.; Kelly, M. J. J. Am. Chem. Soc. 1988, 110, 6432 https://doi.org/10.1021/ja00227a024
  9. Dulcere, J. P.; Agati, V.; Faure, R. Chem. Commun. 1993, 270
  10. Spino, C.; Thibault, C.; Gingras, S. J. Org. Chem. 1998, 63, 5283 https://doi.org/10.1021/jo980482l
  11. Regas, D.; Afonso, M. M.; Rodriguez, M. L.; Palenzuela, J. A. J. Org. Chem. 2003, 68, 7845 https://doi.org/10.1021/jo034480z
  12. Regas, D.; Ruiz, J. M.; Afonso, M. M.; Palenzuela, J. A. J. Org. Chem. 2006, 71, 9153 https://doi.org/10.1021/jo061582r
  13. Murakami, M.; Itami, K.; Ito, Y. Angew. Chem. Int. Ed. 1995, 34, 2691
  14. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 7163 https://doi.org/10.1021/ja970626y
  15. Lee, P. H.; Lee, K. Angew. Chem. Int. Ed. 2005, 44, 3253 https://doi.org/10.1002/anie.200461957
  16. Lee, P. H.; Lee, K.; Kang, Y. J. Am. Chem. Soc. 2006, 128, 1139 https://doi.org/10.1021/ja054144v
  17. Funami, H.; Kusama, H.; Iwasawa, N. Angew. Chem. Int. Ed. 2007, 46, 909 https://doi.org/10.1002/anie.200603986
  18. Cavallito, C. J.; Fruehauf, D. M.; Bailey, J. H. J. Am. Chem. Soc. 1948, 70, 3724 https://doi.org/10.1021/ja01191a052
  19. Lee, K. H.; Hall, I. H.; Mar, E. C.; Starnes, C. O.; El Gebaly, S. A.; Waddell, T. G.; Hadgraft, R. I.; Ruffner, C. G.; Weidner, I. Science 1977, 196, 533 https://doi.org/10.1126/science.191909
  20. Spring, O.; Albert, K.; Gradmann, W. Phytochemistry 1981, 20, 1883 https://doi.org/10.1016/0031-9422(81)84027-7
  21. Park, B. K.; Nakagawa, M.; Hirota, A.; Nakayama, M. J. Antibiot. 1988, 41, 751 https://doi.org/10.7164/antibiotics.41.751
  22. Liu, S.; Liu, H.; Yan, W.; Zhang, L.; Bai, N.; Ho, C.-T. Bioorg. Med. Chem. Lett. 2004, 14, 1101 https://doi.org/10.1016/j.bmcl.2003.12.078
  23. 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

피인용 문헌

  1. An Effective Diels-Alder Reaction of Vinyl Allenols with Dienophiles vol.2011, pp.7, 2011, https://doi.org/10.1002/ejoc.201001148
  2. Organoindium Reagents: The Preparation and Application in Organic Synthesis vol.113, pp.1, 2013, https://doi.org/10.1021/cr300051y
  3. ChemInform Abstract: Synthesis of Cyclic Compounds Having exo-Methylene Groups Through the Diels-Alder Reactions of Vinyl Allenes Obtained from Propargyl Bromide and Indium. vol.39, pp.28, 2008, https://doi.org/10.1002/chin.200828034
  4. Stereoselective Synthesis of 4-Alkyl- or 4-Aryl-3-ethoxycarbonyl-2-halo-1,3-dienes from the Reaction of Allenols Having Ethoxycarbonyl Group with Indium Trihalide vol.30, pp.2, 2008, https://doi.org/10.5012/bkcs.2009.30.2.471
  5. Efficient Preparation of 1,3-Butadiene and Cyclohexene Derivatives Possessing 2-Aminomethyl Group through Indium-Mediated 1,3-Butadien-2-ylation vol.31, pp.2, 2008, https://doi.org/10.5012/bkcs.2010.31.02.503
  6. Efficient Synthetic Method of Z-Selective 2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide vol.31, pp.3, 2008, https://doi.org/10.5012/bkcs.2010.31.03.645
  7. Synthesis of (E)-α-Ethynyl-α,β-unsaturated Esters from Allenyl Acetates Catalyzed by DABCO and Their Application to Sonogashira Cross-Coupling Reactions vol.31, pp.3, 2008, https://doi.org/10.5012/bkcs.2010.31.03.742
  8. Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides vol.32, pp.8, 2008, https://doi.org/10.5012/bkcs.2011.32.8.2911
  9. Copper(I)‐catalyzed Cyclization Reactions of Ethyl ( E )‐α‐Ethynyl‐β‐Aryl‐α,β‐Unsaturated Esters with N ‐Sulfonyl Azides: vol.40, pp.7, 2008, https://doi.org/10.1002/bkcs.11755