Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Organocatalytic Enantioselective Friedel-Crafts Reaction of Naphthol with β,γ-Unsaturated α-Keto Esters

  • Lee, Hyun A (Department of Chemistry, Soonchunhyang University) ;
  • Kim, Dae Young (Department of Chemistry, Soonchunhyang University)
  • Received : 2013.08.16
  • Accepted : 2013.09.03
  • Published : 2013.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. (a) Ellis, G. P.; Lockhart, I. M. The Chemistry of Heterocyclic Compounds, Chromenes,Chromanones, and Chromones; Ellis,G. P., Ed.; Wiley-VCH: New York, 2007; Vol. 31, pp 1-1196.
  2. (b) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. https://doi.org/10.1021/cr020033s
  3. (a) Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 13596. https://doi.org/10.1021/ja046890q
  4. (b) Ulgheri, F.; Marchetti, M.; Piccolo, O. J. Org. Chem. 2007, 72, 6056. https://doi.org/10.1021/jo0705667
  5. (c) Jagdale, A. R.; Sudalai, A. Tetrahedron Lett. 2007, 48, 4895. https://doi.org/10.1016/j.tetlet.2007.05.059
  6. (a) Hayashi, T. Pure. Appl. Chem. 2004, 76, 465. https://doi.org/10.1351/pac200476030465
  7. (b) Paquin, J. F.; Defieber, C.; Stephenson, C. R.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850. https://doi.org/10.1021/ja053270w
  8. (c) Fessard, T. C.; Andrews, S. P.; Motoyoshi, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 9331. https://doi.org/10.1002/anie.200702995
  9. (a) Poulsen, T. B.; Jorgensen, K. A. Chem. Rev, 2008, 108, 2903. https://doi.org/10.1021/cr078372e
  10. (b) You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 210.
  11. (c) Bandini, M.; Umani-Ronchi, A. Catalytic Asymmetric Friedel-Crafts Alkylations; Wiley-VCH: Weinheim, 2009.
  12. (a) Evans, D. A.; Fandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005, 127, 8942. https://doi.org/10.1021/ja052433d
  13. (b) Palomo, C.; Oiarbide, M.; Kardak, B. G.; Garcia J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154. https://doi.org/10.1021/ja0423217
  14. (c) Yang, H.; Hong, Y.-T.; Kim, S. Org. Lett. 2007, 9, 2281. https://doi.org/10.1021/ol070548b
  15. (d) Blay, G.; Fernandez, I.; Pedro, J. R.; Vila, C. Org. Lett. 2007, 9, 2601. https://doi.org/10.1021/ol0710820
  16. (e) Singh, P. K.; Singh, V. K. Org. Lett. 2008, 10, 4121. https://doi.org/10.1021/ol8016929
  17. (a) Cai, C.; Zhao, Z.-A.; You, S.-L. Angew. Chem., Int. Ed. 2009, 48, 7428. https://doi.org/10.1002/anie.200903462
  18. (b) Sheng, Y.-F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899. https://doi.org/10.1021/jo9013029
  19. (c) Jiang, H.; Paixoa, M. W.; Monge, D.; Jorgensen, K. A. J. Am. Chem. Soc. 2010, 132, 2775. https://doi.org/10.1021/ja9097803
  20. (d) Bachu P.; Akiyama, T. Chem. Commun. 2010, 46, 4112. https://doi.org/10.1039/c000862a
  21. (e) Shi, Z.-H.; Sheng, H.; Yang, K.-F.; Jiang, J.-X.; Lai, G.-Q.; Lu, Y.; Xu, L.-W. Eur. J. Org. Chem. 2011, 66.
  22. (a) Wang, X.-S.; Zheng, C.-W.; Zhao, S.-L.; Chai, Z.; Zhao, G.; Yang, G.-S. Tetrahedron: Asymmetry 2008, 19, 2699. https://doi.org/10.1016/j.tetasy.2008.11.025
  23. (b) Jiang, X.; Wu, L.; Xing, Y.; Wang, L.; Wang, S.; Chen, Z.; Wang, R. Chem. Commun. 2012, 48, 446. https://doi.org/10.1039/c1cc14379d
  24. (a) Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847. https://doi.org/10.1021/ja103786c
  25. (b) Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783. https://doi.org/10.1002/adsc.201000515
  26. (c) Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917. https://doi.org/10.2174/138527210791111768
  27. (d) Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2010, 51, 2906. https://doi.org/10.1016/j.tetlet.2010.03.105
  28. (e) Kang, Y. K. Kim, D. Y. Tetrahedron Lett. 2011, 52, 2356. https://doi.org/10.1016/j.tetlet.2011.02.087
  29. (f) Lee, H. J. Kang, S. H.; Kim, D. Y. Synlett 2011, 1559.
  30. (g) Woo, S. B.; Kim, D. Y. Beilstein J. Org. Chem. 2012, 8, 699. https://doi.org/10.3762/bjoc.8.78
  31. (h) Lee, H. J.; Woo, S. B.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3374. https://doi.org/10.1016/j.tetlet.2012.04.095
  32. (i) Moon, H. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2845. https://doi.org/10.5012/bkcs.2012.33.9.2845
  33. (j) Lee, H. J.; Woo, S. B.; Kim, D. Y. Molecules 2012, 17, 7523. https://doi.org/10.3390/molecules17067523
  34. (k) Lee, H. J.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3437. https://doi.org/10.1016/j.tetlet.2012.04.072
  35. (l) Lee, H. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 3171. https://doi.org/10.5012/bkcs.2012.33.10.3171
  36. (m) Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6569. https://doi.org/10.1016/j.tetlet.2012.09.100
  37. (n) Kang, Y. K.; Kim, H. H.; Koh, K. O.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3811. https://doi.org/10.1016/j.tetlet.2012.05.064
  38. (o) Kwon, B. K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2481. https://doi.org/10.5012/bkcs.2012.33.8.2481
  39. (p) Lee, H. J.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6984. https://doi.org/10.1016/j.tetlet.2012.10.051
  40. (q) Lim, Y. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 1825. https://doi.org/10.5012/bkcs.2012.33.6.1825
  41. (r) Kang, Y. K.; Lee, H. J.; Moon, H. W.; Kim, D. Y. RSC Adv. 2013, 3, 1332. https://doi.org/10.1039/c2ra21945j
  42. (s) Lim, Y. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 1955. https://doi.org/10.5012/bkcs.2013.34.7.1955
  43. (t) Woo, S. B.; Suh, C. W.; Koh, K. O.; Kim, D. Y. Tetrahedron Lett. 2013, 54, 3359. https://doi.org/10.1016/j.tetlet.2013.04.054
  44. (u) Suh, C. W.; Chang, C. W.; Choi, K. W.; Lim, Y. J.; Kim, D. Y. Tetrahedron Lett. 2013, 54, 3651. https://doi.org/10.1016/j.tetlet.2013.04.132
  45. (a) Kang, S. H.; Kwon, B. K. Kim, D. Y. Tetrahedron Lett. 2011, 52, 3247. https://doi.org/10.1016/j.tetlet.2011.04.084
  46. (b) Kang, Y. K.; Suh, K. H.; Kim, D. Y. Synlett 2011, 1125.
  47. (c) Kang, Y. K.; Suh, K. H.; Kim, D. Y. Synlett 2011, 1125.
  48. (d) Lee, H. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 3537. https://doi.org/10.5012/bkcs.2012.33.11.3537
  49. (e) Lee, H. J.; Kim, D. Y. Synlett 2012, 1629.
  50. (f) Suh, C. W.; Han, T. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 1623. https://doi.org/10.5012/bkcs.2013.34.6.1623
  51. (g) Lee, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 1619. https://doi.org/10.5012/bkcs.2013.34.6.1619

Cited by

  1. Bifunctional Amine-Squaramides: Powerful Hydrogen-Bonding Organocatalysts for Asymmetric Domino/Cascade Reactions vol.357, pp.2-3, 2015, https://doi.org/10.1002/adsc.201401003
  2. Diastereo- and Enantioselective Conjugate Addition of α-Substituted Cyanoacetates to Maleimides Catalyzed by Binaphthyl-based Thiourea vol.36, pp.9, 2015, https://doi.org/10.1002/bkcs.10439
  3. Asymmetric Michael Addition of Pyrazolones to β,γ-Unsaturated α-Keto Esters Catalyzed by Binaphthyl-modified Thiourea vol.39, pp.4, 2018, https://doi.org/10.1002/bkcs.11425
  4. Forty Years after “Heterodiene Syntheses with α,β-Unsaturated Carbonyl Compounds”: Enantioselective Syntheses of 3,4-Dihydropyran Derivatives vol.118, pp.4, 2013, https://doi.org/10.1021/acs.chemrev.7b00322