Asymmetric organocatalytic N-nitroso-aldol reaction of oxindoles

Tetrahedron Asymmetry

Volumn 21, Issue 23, 2010, Pages 2800-2806

  Zhang, Tao ^a   Cheng, Liang ^a   Liu, Li ^a   Wang, Dong ^a   Chen, Yong Jun ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; NITROSO DERIVATIVE; OXINDOLE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CINCHONA; ENANTIOSELECTIVITY; NONHUMAN; PRIORITY JOURNAL;

EID: 78651393726     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.11.002     Document Type: Article

References (60)

1. For reviews, see: J.M. Janey Angew. Chem., Int. Ed. 44 2005 4292 4300
2. H. Yamamoto, and N. Momiyama Chem. Commun. 2005 3514 3525
3. G. Guillena, and D.J. Ramon Tetrahedron: Asymmetry 17 2006 1465 1492
4. H. Yamamoto, and M. Kawasaki Bull. Chem. Soc. Jpn. 80 2007 595 607
5. F.L.S. Da Machado Synlett 2008 3075 3076
6. H. Yamamoto, S. Saito, and N. Momiyama J. Synth. Org. Chem. Jpn. 66 2008 774 784
7. A. Yanagisawa, and T. Arai Chem. Commun. 2008 1165 1172
8. T. Vilaivan, and W. Bhanthumnavin Molecules 15 2010 917 958
9. For examples, catalyzed by amino acid and its derivatives, see: S.P. Brown, M.P. Brochu, C.J. Sinz, and D.W.C. MacMillan J. Am. Chem. Soc. 125 2003 10808 10809
10. Y. Hayashi, J. Yamaguchi, K. Hibino, and M. Shoji Tetrahedron Lett. 44 2003 8293 8296
11. N. Momiyama, and H. Yamamoto J. Am. Chem. Soc. 125 2003 6038 6039
12. G. Zhong Angew. Chem., Int. Ed. 42 2003 4247 4250
13. A. Bøgevig, H. Sundén, and A. Córdova Angew. Chem., Int. Ed. 43 2004 1109 1112
14. A. Cordova, H. Sunden, A. Bogevig, M. Johansson, and F. Himo Chem. Eur. J. 10 2004 3673 3684
15. Y. Hayashi, J. Yamaguchi, T. Sumiya, K. Hibino, and M. Shoji J. Org. Chem. 69 2004 5966 5973
16. Y. Hayashi, J. Yamaguchi, T. Sumiya, and M. Shoji Angew. Chem., Int. Ed. 43 2004 1112 1115
17. P. Merino, and T. Tejero Angew. Chem., Int. Ed. 43 2004 2995 2997
18. W. Wang, J. Wang, H. Li, and L.X. Liao Tetrahedron Lett. 45 2004 7235 7238
19. Y. Yamamoto, N. Momiyama, and H. Yamamoto J. Am. Chem. Soc. 126 2004 5962 5963
20. D.B. Ramachary, and C.F. Barbas Org. Lett. 7 2005 1577 1580
21. H. Sunden, N. Dahlin, I. Ibrahem, H. Adolfsson, and A. Cordova Tetrahedron Lett. 46 2005 3385 3389
22. H.M. Guo, H.Y. Niu, M.X. Xue, Q.X. Guo, L.F. Cun, A.Q. Mi, Y.Z. Jiang, and J.J. Wang Green Chem. 8 2006 682 684
23. S.G. Kim, and T.H. Park Tetrahedron Lett. 47 2006 9067 9071
24. S.G. Kim, E.J. Ahm, and T.H. Park Bull. Korean Chem. Soc. 28 2007 1665 1669
25. T. Kano, A. Yamamoto, and K. Maruoka Tetrahedron Lett. 49 2008 5369 5371
26. T. Kano, A. Yamamoto, H. Mii, J. Takai, S. Shirakawa, and K. Maruoka Chem. Lett. 37 2008 250 251
27. P.J. Chua, B. Tan, and G.F. Zhong Green Chem. 11 2009 543 547
28. P. Jiao, and H. Yamamoto Synlett 2009 2685 2687
29. T. Kano, A. Yamamoto, F. Shirozu, and K. Maruoka Synthesis 9 2009 1557 1563
30. S.T. Tong, M.A. Brimble, and D. Barker Tetrahedron 65 2009 4801 4807
31. A. Mielgo, I. Velilla, E. Gómez-Bengoa, and C. Palomo Chem. Eur. J. 16 2010 7496 7502
32. X. Ding, W. Tang, C. Zhu, and Y. Cheng Adv. Synth. Catal. 352 2010 108 112
33. For the example catalyzed by the cinchona alkaloid, see: T. Bui, N.R. Candeias, and C.F. Barbas J. Am. Chem. Soc. 132 2010 5574 5575
34. For the example catalyzed by the chiral phosphoric acid, see: G.F. Zhong, M. Lu, D. Zhu, Y.P. Lu, X.F. Zeng, B. Tan, and Z.J. Xu J. Am. Chem. Soc. 131 2009 4562 4563
35. T. Kano, M. Ueda, J. Takai, and K. Maruoka J. Am. Chem. Soc. 128 2006 6046 6047
36. J. Lopez-Cantarero, M.B. Cid, T.B. Poulsen, M. Bella, J.L.G. Ruano, and K.A. Jorgensen J. Org. Chem. 72 2007 7062 7065
37. H.M. Guo, L. Cheng, L.F. Cun, L.Z. Gong, A.Q. Mi, and Y.Z. Jiang Chem. Commun. 2006 429 431
38. C. Palomo, S. Vera, I. Velilla, A. Mielgo, and E. Gomez-Bengoa Angew. Chem., Int. Ed. 46 2007 8054 8056
39. N. Momiyama, and H. Yamamoto J. Am. Chem. Soc. 127 2005 1080 1081
40. For the latest review of 2-oxindoles, see: F. Zhou, Y.-L. Liu, and J. Zhou Adv. Synth. Catal. 352 2010 1381 1407
41. For selected examples, see: P.A.S. Smith J. Am. Chem. Soc. 106 1984 4069 4070
42. S. Hibino, and T. Choshi Nat. Prod. Rep. 18 2001 66 87
43. C. Marti, and E.M. Carreira Eur. J. Org. Chem. 12 2003 2209 2219
44. M. Ochi, K. Kawasaki, H. Kataoka, Y. Uchio, and H. Nishi Biochem. Biophys. Res. Commun. 283 2001 1118 1123
45. S.L.G. Claudine, D. Sylvain, B. Gabrielle, M. Maurice, S. Jacques, G. Rolf, G. Guy, and G. Gilles Stress 6 2003 199 206
46. K. Bernard, S. Bogliolo, and J. Ehrenfeld Br. J. Pharmacol. 144 2005 1037 1050
47. For selected examples, see: H. Miyabe, Y. Yamaoka, and Y. Takemoto J. Org. Chem. 70 2005 3324 3327
48. E.L. Watson, S.P. Marsden, and S.A. Raw Tetrahedron Lett. 50 2009 3318 3320
49. A.F. Bella, A.M.Z. Slawin, and J.C. Walton J. Org. Chem. 69 2004 5926 5933
50. L. Cheng, L. Liu, D. Wang, and Y.J. Chen Org. Lett. 11 2009 3874 3877
51. Full crystallographic data for the structure of 4h have been deposited with the Cambridge Crystallographic Data Centre, as supplementary publication number CCDC 776869.
52. For selected examples catalyzed by 3d, see: Y.-n. Xuan, S.-z. Nie, L.-t. Dong, J.-m. Zhang, and M. Yan Org. Lett. 11 2009 1583 1586
53. S. Gogoi, and C.-G. Zhao Tetrahedron Lett. 50 2009 2252 2255
54. R. Dodda, J.J. Goldman, T. Mandal, C.-G. Zhao, G.A. Broker, and E.R.T. Tiekink Adv. Synth. Catal. 350 2008 537 541
55. T. Mandal, S. Samanta, and C.-G. Zhao Org. Lett. 9 2007 943 945
56. H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B.M. Foxman, and L. Deng Angew. Chem., Int. Ed. 44 2005 105 108
57. H. Li, Y. Wang, L. Tang, and L. Deng J. Am. Chem. Soc. 126 2004 9906 9907
58. J. Deng, S.L. Zhang, P. Ding, H.L. Jiang, W. Wang, and J. Li Adv. Synth. Catal. 352 2010 833 838
59. I.W. Elliott, and P. Rivers J. Org. Chem. 29 1964 2438 2440
60. B.M. Trost, Y. Zhang, and T. Zhang J. Org. Chem. 74 2009 5115 5117