Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones

Tetrahedron Letters

Volumn 53, Issue 3, 2012, Pages 359-362

  Bhanushali, Mayur ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

1H Pyrrole 2,3 dione; 3 Hydroxy 1H pyrrol 2(3H) one; Aldol reaction; Cinchona alkaloid; Enantioselective; Organocatalysis; Proline

Indexed keywords

1H PYRROLE 2,3 DIONE DERIVATIVE; 3 HYDROXY 1H PYRROL 2(3H) ONE DERIVATIVE; AMINE; CINCHONA ALKALOID; CYCLOHEXANONE; PHOSPHATE; PROLINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY;

CINCHONA;

EID: 83555174422     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.056     Document Type: Article

References (70)

1. A. Fürstner Angew. Chem., Int. Ed. 42 2003 3582 3603
2. O.V. Larionov, and A. de Meijere Angew. Chem., Int. Ed. 44 2005 5664 5667
3. G. Dannhardt, and W. Kiefer Arch. Pharm. Pharm. Med. Chem. 334 2001 183 188
4. T. Lindel, M. Hochgürtel, M. Assmann, and M. Köck J. Nat. Prod. 63 2000 1566 1569
5. S. Depraetere, W. Smet, and M. Dehaen Angew. Chem., Int. Ed. 38 1999 3359 3361
6. J.M. Gottesfeld, L. Neely, J.W. Trauger, E.E. Baird, and P.B. Dervan Nature 387 1997 202 205
7. V.L. Gein, E.V. Voronina, T.E. Ryumina, G.N. Novoselova, K.D. Potemkin, and Yu.S. Andreichikov Khim. Farm. Zh. 30 1996 25 26
8. M.D. Parenti, S. Pacchioni, A.M. Ferrari, and G. Rastelli J. Med. Chem. 47 2004 4258 4267
9. B.L. Mylari, T.A. Beyer, and T.W. Siegel J. Med. Chem. 34 1991 1011 1018
10. E.K. Lee, W.T. Regenold, and P. Shapiro Anti-cancer Drugs 13 2002 859 868
11. N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, and G. Marandi ARKIVOC 2008 282 288
12. For reviews on organocatalytic aldol reactions, see: X.-H. Chen, J. Yu, and L.-Z. Gong Chem. Commun. 46 2010 6437 6448
13. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471 5569
14. W. Notz, F. Tanaka, and C.F. Barbas III Acc. Chem. Res. 37 2004 580 591
15. B. List Acc. Chem. Res. 37 2004 548 557
16. B. List Tetrahedron 58 2002 5573 5590
17. H. Pellissier Tetrahedron 63 2007 9267 9331
18. S. Samanta, and C.-G. Zhao J. Am. Chem. Soc. 128 2006 7442 7443
19. R. Dodda, and C.-G. Zhao Org. Lett. 8 2006 4911 4914
20. T. Mandal, S. Samanta, and C.-G. Zhao Org. Lett. 9 2007 943 945
21. S. Samanta, S. Perera, and C.-G. Zhao J. Org. Chem. 75 2010 1101 1106
22. R. Dodda, and C.-G. Zhao Synlett 2007 1605 1609
23. Q. Guo, M. Bhanushali, and C.-G. Zhao Angew. Chem., Int. Ed. 49 2010 9460 9464
24. S. Perera, V. Naganaboina, L. Wang, B. Zhang, Q. Guo, L. Rout, and C.-G. Zhao Adv. Syn. Catal. 353 2011 1729 1734
25. J. Guang, and C.-G. Zhao Tetrahedron: Asymmetry 22 2011 1205 1211
26. For a review, see: M. Bhanushali, and C.-G. Zhao Synthesis 2011 1815 1830
27. For examples, see: G. Luppi, P.G. Cozzi, M. Monari, B. Kaptein, Q.B. Broxterman, and C. Tomasini J. Org. Chem. 70 2005 7418 7421
28. Z. Shen, B. Li, L. Wang, and Y. Zhang Tetrahedron Lett. 46 2005 8785 8788
29. D. Enders, and C. Grondal Angew. Chem., Int. Ed. 44 2005 1210 1212
30. O. Tokuda, T. Kano, W.-G. Gao, T. Ikemoto, and K. Maruoka Org. Lett. 7 2005 5103 5105
31. S. Samanta, and C.-G. Zhao Tetrahedron Lett. 47 2006 3383 3386
32. Z. Tang, L.-F. Cun, X. Cui, A.-Q. Mi, Y.-Z. Jiang, and L.-Z. Gong Org. Lett. 8 2006 1263 1266
33. J. Liu, Z. Yang, Z. Wang, F. Wang, X. Chen, X. Liu, X. Feng, Z. Su, and C. Hu J. Am. Chem. Soc. 130 2008 5654 5655
34. J. Jiang, X. Chen, J. Wang, Y. Hui, X. Liu, L. Lin, and X. Feng Org. Biomol. Chem. 7 2009 4355 4357
35. T. Urushima, Y. Yasui, H. Ishikawa, and Y. Hayashi Org. Lett. 12 2010 2966 2969
36. S. Allu, N. Molleti, R. Panem, and V.K. Singh Tetrahedron Lett. 52 2011 4080 4083
37. T. Sano, Y. Horiguchi, J. Toda, K. Imafuku, and Y. Tsuda Chem. Pharm. Bull. 32 1984 497 503
38. F. Giacalone, M. Gruttadauria, P. Lo Meo, S. Riela, and R. Noto Adv. Synth. Catal. 350 2008 2747 2760
39. S. Aratake, T. Itoh, T. Okano, N. Nagae, T. Sumiya, M. Shoji, and Y. Hayashi Chem. Eur. J. 13 2007 10246 10256
40. For selected examples, see: J.G. Hernandez, and E. Juaristi Tetrahedron 67 2011 6953 6959
41. T. Miura, M. Ina, K. Imai, K. Nakashima, Y. Yasaku, N. Koyata, Y. Murakami, N. Imai, N. Tada, and A. Itoh Tetrahedron: Asymmetry 22 2011 1028 1034
42. A. Kumar, S. Singh, V. Kumar, and S. Singh Chimni Org. Biomol. Chem. 9 2011 2731 2742
43. Y. Hayashi, Y. Yasui, T. Kawamura, M. Kojima, and H. Ishikawa Angew. Chem., Int. Ed. 50 2011 2804 2807
44. Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, and M. Shoji Angew. Chem., Int. Ed. 45 2006 958 961
45. Y.-Q. Fu, Y.-J. An, W.-M. Liu, Z.-C. Li, G. Zhang, and J.C. Tao Catal. Lett. 124 2008 397 404
46. F. Giacalone, M. Gruttadauria, P.L. Meo, S. Riela, and R. Noto Adv. Synth. Catal. 350 2008 2747 2760
47. D. Font, S. Sayalero, A. Bastero, C. Jimeno, and M.A. Perics Org. Lett. 10 2008 337 340
48. Y.-X. Liu, Y.-N. Sun, H.-H. Tan, W. Liu, and J.-C. Tao Tetrahedron: Asymmetry 18 2007 2649 2656
49. M. Raj, V. Maya, S.K. Ginotra, and V.K. Singh Org. Lett. 8 2006 4097 4099
50. F.-Z. Peng, Z.-H. Shao, X.-W. Pu, and H.-B. Zhang Adv. Synth. Catal. 350 2008 2199 2204
51. Y.-Q. Fu, Z.-C. Li, L.-N. Ding, J.-C. Tao, S.-H. Zhang, and M.-S. Tang Tetrahedron: Asymmetry 17 2006 3351 3357
52. N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, and C.F. Barbas III J. Am. Chem. Soc. 128 2006 734 735
53. L. Zu, H. Xie, H. Li, J. Wang, and W. Wang Org. Lett. 10 2008 1211 1214
54. For a review, see: M. Gruttadauria, F. Giacalone, and R. Noto Adv. Synth. Catal. 351 2009 33 57
55. For selected examples of primary amine catalyzed reactions, see: C.M. Reisinger, X. Wang, and B. List Angew. Chem., Int. Ed. 47 2008 8112 8115
56. N.J.A. Martin, and B. List J. Am. Chem. Soc. 128 2006 13368 13369
57. X. Lu, Y. Liu, B. Sun, B. Cindric, and L. Deng J. Am. Chem. Soc. 130 2008 8134 8135
58. X. Wang, C.M. Reisinger, and B. List J. Am. Chem. Soc. 130 2008 6070 6071
59. S.H. McCooey, and S.J. Connon Org. Lett. 9 2007 599 602
60. T.-Y. Liu, H.-L. Cui, Y. Zhang, K. Jiang, W. Du, Z.-Q. He, and Y.-C. Chen Org. Lett. 9 2007 3671 3674
61. J. Zhou, V. Wakchaure, P. Kraft, and B. List Angew. Chem., Int. Ed. 47 2008 7656 7658
62. S. Gogoi, C.-G. Zhao, and D. Ding Org. Lett. 11 2009 2249 2252
63. T. Mandal, and C.-G. Zhao Angew. Chem., Int. Ed. 47 2008 7714 7717
64. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, and J.-G. Deng Angew. Chem., Int. Ed. 46 2007 389 392
65. H. Huang, and E.N. Jacobsen J. Am. Chem. Soc. 128 2006 7170 7171
66. O. Lifchits, C.M. Reisinger, and B. List J. Am. Chem. Soc. 132 2010 10227 10229
67. X. Zhu, A. Lin, Y. Shi, J. Guo, C. Zhu, and Y. Cheng Org. Lett. 13 2011 4382 4385
68. C. Liu, Q. Zhu, K.-W. Huang, and Y. Lu Org. Lett. 13 2011 2638 2641
69. For reviews on primary amine catalysis, see: F. Peng, and Z. Shao J. Mol. Catal. A 285 2008 1 13
70. J.B. Brazier, and N.C.O. Tomkinson Top. Curr. Chem. 291 2010 281 347