Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Efficient Preparation of 1,3-Butadiene and Cyclohexene Derivatives Possessing 2-Aminomethyl Group through Indium-Mediated 1,3-Butadien-2-ylation

  • SeoMoon, Dong (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Mo, Jun-Tae (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Kang, Dong-Jin (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University) ;
  • Eom, Da-Han (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 : 2010.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. https://doi.org/10.1016/S0957-4166(97)00208-5
  2. Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. https://doi.org/10.1039/a827013z
  3. Job, A.; Janeck, C. F.; Bettray,W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253. https://doi.org/10.1016/S0040-4020(02)00080-7
  4. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. https://doi.org/10.1021/ar020066u
  5. Alvaro, G.; Savoia, D. Synlett 2002, 651.
  6. Zhou, P.; Chen, B.; Davis, F. A. Tetrahedron 2004, 60, 8003. https://doi.org/10.1016/j.tet.2004.06.071
  7. Friestad, G. K. Eur. J. Org. Chem. 2005, 3157.
  8. Beuchet, P.; Marrec, N. L.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959. https://doi.org/10.1016/S0040-4039(00)61099-7
  9. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. https://doi.org/10.1021/cr00022a010
  10. Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronichi, A. J. Org. Chem. 1994, 59, 7766. https://doi.org/10.1021/jo00104a037
  11. Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605. https://doi.org/10.1016/S0040-4039(98)01926-1
  12. Bloch, R. Chem. Rev. 1998, 98, 1407. https://doi.org/10.1021/cr940474e
  13. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. https://doi.org/10.1021/cr980414z
  14. Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589. https://doi.org/10.1021/jo0009898
  15. Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467. https://doi.org/10.1021/jo0018038
  16. Yanada, R.; Kaieda, A.; Takemoto, Y. J. Org. Chem. 2001, 66, 7516. https://doi.org/10.1021/jo015719j
  17. Lee, J. G.; Choi, K. I.; Pae, A. N.; Koh, H. Y.; Kang, Y.; Cho, Y. S. J. Chem. Soc., Perkin Trans. 1 2002, 1314.
  18. Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2004, 69, 1415. https://doi.org/10.1021/jo035442i
  19. Yamada, K.-I.; Tomioka, K. Chem. Rev. 2008, 108, 2874. https://doi.org/10.1021/cr078370u
  20. Hosomi, A.; Masunari, T.; Tominaga, Y.; Hojo, M. Bull. Chem. Soc. Jpn. 1991, 64, 1051. https://doi.org/10.1246/bcsj.64.1051
  21. Sheares, V. V.; Wu, L.; Li, Y.; Emmick, T. K. J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 4070. https://doi.org/10.1002/1099-0518(20001115)38:22<4070::AID-POLA70>3.0.CO;2-P
  22. Jones, G. D.; Meyer, W. C.; Tefertiller, N. B.; Macwilliams, D. C. J. Polym. Sci. 1970, 8, 2123. https://doi.org/10.1002/pol.1970.150080820
  23. Coulson, D. R. J. Org. Chem. 1973, 38, 1483. https://doi.org/10.1021/jo00948a009
  24. Castagnolo, D.; Renzulli, M. L.; Galletti, E.; Corelli, F.; Botta, M. Tetrahedron: Asymmetry 2005, 16, 2893. https://doi.org/10.1016/j.tetasy.2005.08.002
  25. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, U.K., 1990.
  26. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 315.
  27. Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. https://doi.org/10.1016/S0040-4020(97)00747-3
  28. Marsault, E.; Toro, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243. https://doi.org/10.1016/S0040-4020(01)00121-1
  29. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem. Int. Ed. 2002, 41, 1668. https://doi.org/10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z
  30. Li, C.-J. Chem. Rev. 1993, 93, 2023. https://doi.org/10.1021/cr00022a004
  31. Li, C.-J. Tetrahedron 1996, 52, 5643. https://doi.org/10.1016/0040-4020(95)01056-4
  32. Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
  33. Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149. https://doi.org/10.1016/S0040-4020(99)00641-9
  34. A, J. M.; Lee, P. H. Bull. Korean Chem. Soc. 2009, 30, 471. https://doi.org/10.5012/bkcs.2009.30.2.471
  35. Lee, P. H.; Sung, S.-Y.; Lee, K. Org. Lett. 2001, 3, 3201. https://doi.org/10.1021/ol016532h
  36. Seomoon, D.; Lee, K.; Kim, H.; Lee, P. H. Chem. Eur. J. 2007, 13, 5197. https://doi.org/10.1002/chem.200601338
  37. Lee, K; Lee, J.; Lee, P. H. J. Org. Chem. 2002, 67, 8265. https://doi.org/10.1021/jo026121u
  38. Lee, P. H.; Sung, S.-Y.; Lee, K.; Chang, S. Synlett 2002, 146.
  39. Lee, P. H.; Seomoon, D.; Lee, K.; Kim, S.; Kim, H.; Kim, H.; Shim, E.; Lee, M.; Lee, S.; Kim, M.; Sridhar, M. Adv. Synth. Catal. 2004, 346, 1641. https://doi.org/10.1002/adsc.200404125
  40. Lee, J.-Y.; Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 1929. https://doi.org/10.5012/bkcs.2007.28.11.1929
  41. Seomoon, D.; Lee, P. H. J. Org. Chem. 2008, 73, 1165. https://doi.org/10.1021/jo702279t
  42. 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
  43. Lee, P. H.; Lee, K. Angew. Chem. Int. Ed. 2005, 44, 3253. https://doi.org/10.1002/anie.200461957
  44. Lee, P. H.; Lee, K.; Kang, Y. J. Am. Chem. Soc. 2006, 128, 1139. https://doi.org/10.1021/ja054144v
  45. Lee, K.; Lee, P. H. Bull. Korean Chem. Soc. 2008, 29, 487. https://doi.org/10.5012/bkcs.2008.29.2.487
  46. Perez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155. https://doi.org/10.1021/ja004195m
  47. Lee, P. H.; Lee, S. W.; Lee, K. Org. Lett. 2003, 5, 1103. https://doi.org/10.1021/ol034167j
  48. Lee, W.; Kang, Y.; Lee, P. H. J. Org. Chem. 2008, 73, 4326. https://doi.org/10.1021/jo800438n
  49. Kim, D.-H.; Hong, C.-K.; Lee, P. H.; Kang, Y. Bull. Korean Chem. Soc. 2008, 29, 2270. https://doi.org/10.5012/bkcs.2008.29.11.2270
  50. Lee, P. H.; Lee, S. W.; Seomoon, D. Org. Lett. 2003, 5, 4963. https://doi.org/10.1021/ol035883o
  51. Lee, S. W.; Lee, K.; Seomoon, D.; Kim, S.; Kim, H.; Kim, H.; Shim, E.; Lee, M.; Lee, S.; Kim, M.; Lee, P. H. J. Org. Chem. 2004, 69, 4852. https://doi.org/10.1021/jo0495790
  52. Lee, J.; Lee, P. H. J. Org. Chem. 2008, 73, 7413. https://doi.org/10.1021/jo801169h
  53. Iwasawa, N.; Miura, T.; Kiyota, K.; Kusami, H.; Lee, K.; Lee, P. H. Org. Lett. 2002, 4, 4463. https://doi.org/10.1021/ol026993i
  54. Miura, T.; Kiyota, K.; Kusama, H.; Lee, K.; Kim, H.; Kim, S.; Lee, P. H.; Iwasawa, N. Org. Lett. 2003, 5, 1725. https://doi.org/10.1021/ol034365a
  55. Lee, K.; Kim, H.; Miura, T.; Kiyota, K.; Kusama, H.; Kim, S.; Iwasawa, N.; Lee, P. H. J. Am. Chem. Soc. 2003, 125, 9682. https://doi.org/10.1021/ja035988m
  56. Aufdermarsh, Jr. C. A. J. Org. Chem. 1964, 29, 1994. https://doi.org/10.1021/jo01030a084
  57. Nunomoto, S. J. Org. Chem. 1979, 44, 4788. https://doi.org/10.1021/jo00394a009
  58. Lu, W.; Ma, J.; Yang, Y.; Chan, T.-H. Org. Lett. 2000, 2, 3469. https://doi.org/10.1021/ol000239k
  59. Kim, S.; Seomoon, D.; Lee, P. H. Chem. Commun. 2009, 1873.
  60. Seomoon, D.; A, J.; Lee, P. H. Org. Lett. 2009, 11, 2401. https://doi.org/10.1021/ol9005213
  61. Johnson, A. W. J. Chem. Soc. 1946, 1009. https://doi.org/10.1039/jr9460001009

Cited by

  1. Palladium-Catalyzed Allyl Cross-Coupling Reactions with In Situ Generated Organoindium Reagents vol.6, pp.8, 2011, https://doi.org/10.1002/asia.201000890
  2. Organoindium Reagents: The Preparation and Application in Organic Synthesis vol.113, pp.1, 2013, https://doi.org/10.1021/cr300051y
  3. α-Imino Esters in Organic Synthesis: Recent Advances vol.117, pp.12, 2017, https://doi.org/10.1021/acs.chemrev.7b00064
  4. ChemInform Abstract: Efficient Preparation of 1,3-Butadiene and Cyclohexene Derivatives Possessing 2-Aminomethyl Group Through Indium-Mediated 1,3-Butadien-2-ylation. vol.41, pp.30, 2010, https://doi.org/10.1002/chin.201030065
  5. 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, 2010, https://doi.org/10.5012/bkcs.2011.32.8.2911
  6. Palladium‐Catalyzed Decarboxylative Generation and Propargylation of 2‐Azaallyl Anions vol.2019, pp.24, 2010, https://doi.org/10.1002/ejoc.201900537
  7. Asymmetric Petasis reaction for the synthesis of chiral α- and β-butadienyl amines vol.57, pp.19, 2010, https://doi.org/10.1039/d0cc08241d