Asymmetric synthesis of highly functionalized γ-lactams through an organocatalytic aza-Michael-Michael reaction cascade using fumaric acid amide esters as multi-reactive substrates

Tetrahedron Letters

Volumn 53, Issue 10, 2012, Pages 1245-1248

  Yokosaka, Takuya ^a   Hamajima, Akinari ^a   Nemoto, Tetsuhiro ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Cascade catalysis; Lactam; Michael reaction; Organocatalyst

Indexed keywords

AMIDE; FUMARIC ACID; FUMARIC ACID AMIDE ESTER; GAMMA LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPIMERIZATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84856498153     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.114     Document Type: Article

References (71)

1. For reviews on asymmetric cascade catalysis, see: C. Grondal, M. Jeanty, and D. Enders Nat. Chem. 2 2010 167 178
2. B. Westermann, M. Ayaz, and S.S. van Berkel Angew. Chem., Int. Ed. 49 2010 846 849
3. J. Zhou Chem. Asian J. 5 2010 422 434
4. Y. Xinhong, and W. Wang Org. Biomol. Chem. 6 2008 2037 2046
5. D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570 1581
6. A.M. Walji, and D.W.C. MacMillan Synlett 2007 1477 1489
7. For recent selected examples, see: R. Okamoto, E. Okazaki, K. Noguchi, and K. Tanaka Org. Lett. 13 2011 4894 4897
8. X.-F. Wang, J.-R. Chen, Y.-J. Cao, H.-G. Cheng, and W.-J. Xiao Org. Lett. 12 2010 1140 1143
9. W. Yao, L. Pan, Y. Wu, and C. Ma Org. Lett. 12 2010 2422 2425
10. W.-B. Chen, Z.-J. Wu, Q.-L. Pei, L.-F. Cun, X.-M. Zhang, and W.-C. Yuan Org. Lett. 12 2010 3132 3135
11. G. Bencivenni, L.Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.P. Song, G. Bartoli, and P. Melchiorre Angew. Chem., Int. Ed. 48 2009 7200 7203
12. W. He, K.-T. Yip, N.-Y. Zhu, and D. Yang Org. Lett. 11 2009 5626 5628
13. J. Zhou, and B. List J. Am. Chem. Soc. 129 2007 7498 7499
14. J.W. Yang, M.Y. Hechavarria Fonseca, and B. List J. Am. Chem. Soc. 127 2005 15036 15037
15. Y. Huang, A.M. Walji, C.H. Larsen, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 15051 15053
16. M. Marigo, J. Franzen, T.B. Poulsen, W. Zhuang, and K.A. Jørgensen J. Am. Chem. Soc. 127 2005 6964 6965
17. For recent selected examples, see: K.E. Ozboya, and T. Rovis Chem. Sci. 2 2011 1835 1838
18. C.B. Jacobsen, K.L. Jensen, J. Udmark, and K.A. Jørgensen Org. Lett. 13 2011 4790 4793
19. D. Enders, A. Grossmann, H. Huang, and G. Raabe Eur. J. Org. Chem. 2011 4298 4301
20. Y. Wang, D.-F. Yu, Y.-Z. Liu, H. Wei, Y.-C. Luo, D.J. Dixon, and P.-F. Xu Chem. Eur. J. 16 2010 3922 3925
21. G.-L. Zhao, F. Ullah, L. Deiana, S. Lin, Q. Zhang, J. Sun, I. Ibrahem, P. Dziedzic, and A. Córdova Chem. Eur. J. 16 2010 1585 1591
22. C.M. Filloux, S.P. Lathrop, and T. Rovis Proc. Natl. Acad. Sci. U.S.A. 107 2010 20666 20671
23. C. Yu, Y. Zhang, S. Zhang, J. He, and W. Wang Tetrahedron Lett. 51 2010 1742 1744
24. S.P. Lathrop, and T. Rovis J. Am. Chem. Soc. 131 2009 13628 13630
25. M.E. Muratore, C.A. Holloway, A.W. Pilling, R.I. Storer, G. Trevitt, and D.J. Dixon J. Am. Chem. Soc. 131 2009 10796 10797
26. Y. Wang, R.-G. Han, Y.-L. Zhou, S. Yang, P.-F. Xu, and D.J. Dixon Angew. Chem., Int. Ed. 48 2009 9834 9838
27. B. Simmons, A.M. Walji, and D.W.C. MacMillan Angew. Chem., Int. Ed. 48 2009 4349 4353
28. Y. Chi, S.T. Scroggins, and J.M.J. Fréchet J. Am. Chem. Soc. 130 2008 6322 6323
29. For recent selected examples of asymmetric synthesis of highly functionalized organic molecules using chiral secondary amine-catalyzed asymmetric cascade catalysis, see: S.B. Jones, B. Simmons, A. Mastracchio, and D.W.C. MacMillan Nature 475 2011 183 188
30. Ł. Albrecht, A. Albrecht, L.K. Ransborg, and K.A. Jørgensen Chem. Sci. 2 2011 1273 1277
31. H. Li, J. Zhao, L. Zeng, and W. Hu J. Org. Chem. 76 2011 8064 8069
32. C. Grondal, M. Jeanty, and D. Enders Nat. Chem. 2 2010 167 178
33. N.T. Jui, E.C.Y. Lee, and D.W.C. MacMillan J. Am. Chem. Soc. 132 2010 10015 10017
34. D. Enders, C. Wang, M. Mukanova, and A. Greb Chem. Commun. 46 2010 2447 2449
35. B.P. Bondzic, T. Urushima, H. Ishikawa, and Y. Hayashi Org. Lett. 12 2010 5434 5437
36. K. Jiang, Z.-J. Jia, X. Yin, L. Wu, and Y.-C. Chen Org. Lett. 12 2010 2766 2769
37. J.-Y. Bae, H.-J. Lee, S.-H. Youn, S.-H. Kwon, and C.-W. Cho Org. Lett. 12 2010 4352 4355
38. B.-C. Hong, P. Kotame, C.-W. Tsai, and J.-H. Liao Org. Lett. 12 2010 776 779
39. L. Hong, W. Sun, C. Liu, L. Wang, and R. Wang Chem. Eur. J. 16 2010 440 444
40. E. Reyes, G. Talavera, J.L. Vicario, D. Badía, and L. Carrillo Angew. Chem., Int. Ed. 48 2009 5701 5704
41. P.G. McGarraugh, and S.E. Brenner Org. Lett. 11 2009 5654 5657
42. J. Wang, H. Li, H.-X. Xie, L.-S. Zu, X. Shen, and W. Wang Angew. Chem., Int. Ed. 46 2007 9050 9053
43. A. Carlone, S. Cabrera, M. Marigo, and K.A. Jørgensen Angew. Chem., Int. Ed. 46 2007 1101 1104
44. M. Rueping, A. Kuenkel, F. Tato, and J.W. Bats Angew. Chem., Int. Ed. 48 2009 3699 3702
45. H. Ishikawa, T. Suzuki, and Y. Hayashi Angew. Chem., Int. Ed. 48 2009 1304 1307
46. Y. Hayashi, M. Toyoshima, H. Gotoh, and H. Ishikawa Org. Lett. 11 2009 45 48
47. H. Li, L. Zu, H. Xie, J. Wang, and W. Wang Chem. Commun. 2008 5636 5638
48. Hexin Xie, L. Zu, H. Li, J. Wang, and W. Wang J. Am. Chem. Soc. 129 2007 10886 10894
49. J.L. Vicario, S. Reboredo, D. Badia, and L. Carrello Angew. Chem., Int. Ed. 46 2007 5168 5170
50. J. Vesely, I. Ibrahem, G.-L. Zhao, R. Rios, and A. Córdova Angew. Chem., Int. Ed. 46 2007 778 781
51. H. Sundén, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, and A. Córdova Adv. Synth. Catal. 349 2007 827 832
52. H. Sundén, I. Ibrahem, G.-L. Zhao, L. Eriksson, and A. Córdova Chem. Eur. J. 13 2007 574 581
53. D.B. Ramachary, and M. Kishor J. Org. Chem. 72 2007 5056 5068
54. D. Enders, M.R.M. Hüttl, C. Grondal, and G. Raabe Nature 441 2006 861 863
55. For recent selected examples of asymmetric synthesis of functionalized γ-lactams, see: X. Zhao, D.A. DiRocco, and T. Rovis J. Am. Chem. Soc. 133 2011 12466 12469
56. N. Satoh, S. Yokoshima, and T. Fukuyama Org. Lett. 13 2011 3028 3031
57. H. Nguyen, G. Ma, T. Gladysheva, T. Fremgen, and D. Romo J. Org. Chem. 76 2011 2 12
58. T.B. Bisol, A.J. Bortoluzzi, and M.M. Sá J. Org. Chem. 76 2011 948 962
59. W. Gu, and R.B. Silverman J. Org. Chem. 76 2011 8287 8293
60. A. Shen, M. Liu, Z.-S. Jia, M.-H. Xu, and G.-Q. Lin Org. Lett. 12 2010 5154 5157
61. E. Forró, and F. Fülöp Eur. J. Org. Chem. 2008 5263 5268
62. E.P. Balskus, and E.N. Jacobsen J. Am. Chem. Soc. 128 2006 6810 6812
63. N. Fukuda, K. Sasaki, T.V.R.S. Sastry, M. Kanai, and M. Shibasaki J. Org. Chem. 71 2006 1220 1225
64. L.R. Reddy, J.-F. Fournier, B.V. Subba Reddy, and E.J. Corey J. Am. Chem. Soc. 127 2005 8974 8976
65. For reviews on the asymmetric synthesis using chiral secondary amine derivatives as organocatalysts, see: M. Nielsen, D. Worgull, T. Zweifel, B. Gschwend, S. Bertelsen, and K.A. Jørgensen Chem. Commun. 47 2011 632 649
66. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178 2189
67. P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli Angew. Chem., Int. Ed. 47 2008 6138 6171
68. A. Mielgo, and C. Palomo Chem. Asian J. 3 2008 922 948
69. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471 5569
70. G. Lelais, and D.W.C. MacMillan K. Mikami, M. Lautens, New Frontiers in Asymmetric Catalysis 2007 Wiley New York 313 358
71. G. Lelais, and D.W.C. MacMillan Aldrichim. Acta 39 2006 79 87