Organocatalytic asymmetric michael addition of 1,3-Cyclohexanedione to benzylidenemalonitriles

Bulletin of the Korean Chemical Society

Volumn 35, Issue 1, 2014, Pages 98-102

  Suh, Chang Won ^a   Kim, Dae Young ^a  

^a Soonchunhyang University   (South Korea)

Author keywords

2 Amino 4H chromenes; Asymmetric catalysis; Michael addition; Organocatalysis

Indexed keywords

1 ,3-CYCLOHEXANEDIONE; 2-AMINO-4H-CHROMENES; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE MICHAEL ADDITION; FACILE SYNTHESIS; MICHAEL ADDITIONS; ORGANOCATALYSIS; ORGANOCATALYTIC;

CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS;

ADDITION REACTIONS;

EID: 84892935255     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2014.35.1.98     Document Type: Article

References (68)

1. Curini, M.; Cravotto, G.; Epofano, F.; Giannone, G. Curr. Med. Chem. 2006, 13, 199.
2. Litvinov, Y. M.; Shestopalov, A. M. Adv. Heterocycl. Chem. 2011, 103, 175. 2.
3. Patchett, A. A.; Nargund, R. P. Ann. Rep. Med. Chem. 2000, 35, 289.
4. Xie, J. W.; Yue, L.; Chen, W.; Du, W.; Zhu, J.; Deng, J. G.; Chen, Y. C. Org. Lett. 2007, 9, 413.
5. Xu, D.-Q.; Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhong, A.-G.; Xia, A.-B.; Xu, Z.-Y. Chem. Eur. J. 2010, 16, 4177. 3.
6. Leonard, J. Contemp. Org. Synth. 1994, 1, 387.
7. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
8. For recent reviews of asymmetric Michael reactions, see: (a) Krause, N. Hoffmann-Röder, A. Synthesis 2001, 171.
9. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
10. Christoffers, J.; Baro, A. Angew. Chem. Int. Ed. 2003, 42, 1688.
11. For selected examples: (a) Wu, F.; Li, H.; Hong, R.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 947.
12. Rueping, M.; Merino, E. Angew. Chem., Int. Ed. 2008, 47, 3046.
13. Yang, J.; Li, W.; Jin, Z.; Liang, X.; Ye, J. Org. Lett. 2010, 12, 5218.
14. Zhang, G.; Wang, Y.; Zhang, W.; Xu, X.; Zhong, A.; Xu, D. Eur. J. Org. Chem. 2011, 2142.
15. Dong, Z.; Liu, X.; Feng, J.; Wang, M.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2011, 137. 6.
16. Gao, Y.; Du, D.-M. Tetrahedron:Asymmetry 2012, 23, 1343.
17. Zhang, G.; Zhang, Y.; Yan, J.; Chen, R.; Wang, S.; Ma, Y.; Wang, R. J. Org. Chem. 2012, 77, 878.
18. Chen, W.-B.; Wu, Z.-J.; Pei, Q.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2010, 12, 3132.
19. For selected examples, see: (a) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.
20. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897.
21. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309.
22. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115.
23. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
24. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779.
25. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847.
26. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2010, 51, 2906 (i) Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917.
27. Kang, S. H.; Kwon, B. K.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 3247.
28. Kang, Y. K.; Suh, K. H.; Kim, D. Y. Synlett 2011, 1125.
29. Moon, H. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 291.
30. Lee, H. J.; Chae, Y. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 2875.
31. Lee, H. J.; Kang, S. H.; Kim, D. Y. Synlett 2011, 1559.
32. Lee, H. J.; Kang, S. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 1125.
33. Lee, H. J.; Kim, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 785.
34. Kang, Y. K.; Kim, H. H.; Koh, K. O.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3811.
35. Kwon, B. K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2481.
36. Lee, H. J.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6984.
37. Lee, H. J.; Woo, S. B.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3374.
38. Moon, H. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2845.
39. Lee, H. J.; Woo, S. B.; Kim, D. Y. Molecules 2012, 17, 7523.
40. w) Lee, H. J.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6984.
41. Lim, Y. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 1955.
42. Woo, S. B.; Suh, C. W.; Koh, K. O.; Kim, D. Y. Tetrahedron Lett. 2013, 54, 3359.
43. Kang, Y. K.; Lee, H. J.; Moon, H. W.; Kim, D. Y. RSC Advances 2013, 3, 1332. 8.
44. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.
45. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.
46. Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2091.
47. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 249.
48. Oh, Y. Y.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4674.
49. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259.
50. Kwon, B. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1441.
51. Kwon, B. K.; Kim, S. M.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 759.
52. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734.
53. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783.
54. Lee, J. H.; Kim, D. Y. Synthesis 2010, 1860.
55. Yoon, S. J.; Kang, Y. K.; Kim, D. Y. Synlett. 2011, 420.
56. Kang, Y. K.; Yoon, S. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 1195.
57. Kang, Y. K. Kim, D. Y. Tetrahedron Lett. 2011, 52, 2356.
58. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 6569.
59. Lee, H. J.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2012, 53, 3437.
60. Lim, Y. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 1825.
61. Lee, H. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 3537.
62. Woo, S. B.; Kim, D. Y. Beilstein J. Org. Chem. 2012, 8, 699.
63. Lee, H. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 3171.
64. Lee, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 1619.
65. Suh, C. W.; Han, T. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 1623.
66. w) Lee, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 2569.
67. Suh, C. W.; Chang, C. W.; Choi, K. W.; Lim, Y. J.; Kim, D. Y. Tetrahedron Lett. 2013, 54, 3651.
68. Lee, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2013, 34, 2569.