Novel chiral ammonium ionic liquids as efficient organocatalysts for asymmetric Michael addition of aldehydes to nitroolefins

Tetrahedron

Volumn 66, Issue 27-28, 2010, Pages 4970-4976

  Wang, Wan Hui ^a   Wang, Xiang Bo ^a   Kodama, Koichi ^a   Hirose, Takuji ^a   Zhang, Guang You ^b  

^a SAITAMA UNIVERSITY   (Japan)

^b UNIVERSITY OF JINAN   (China)

Author keywords

1,3 Diamine; Asymmetric Michael addition; Chiral ammonium ionic liquid

Indexed keywords

2 ((DIMETHYLAMINO)METHYL)CYCLO HEXANAMINE; 2 (1 (2 METHYLPHENYL) 2 NITROETHYL)PENTANAL; 2 (1 (4 BROMOPHENYL) 2 NITROETHYL)PENTANAL; 2 (1 (4 METHOXYPHENYL) 2 NITROETHYL)PENTANAL; 2 (1 (4 METHYLPHENYL) 2 NITROETHYL)PENTANAL; 2 (2 NITRO 1 PHENYLETHYL)HEXANAL; 2 (2 NITRO 1 PHENYLETHYL)PENTANAL; 2 92 NITRO 1 PHENYLETHYL)HEXANAL; 2 BENZAMIDOCYCLOHEXANECARBOXYLIC ACID; 2 ETHYL 4 NITRO 3 PHENYLBUTANAL; 2 ISOPROPYL 4 NITRO PHENYLBUTANAL; 2 METHYL 3 (2 METHYLPHENYL) 4 NITROBUTANAL; 2 METHYL 3 (4 METHYLPHENYL) 4 NITROBUTANAL; 2 METHYL 4 NITRO 3 (THIEN 2 YL) BUTANAL; 2 METHYL 4 NITRO 3 PHENYLBUTANAL; 3 (4 BROMOPHENYL) 2 METHYL 4 NITROBUTANAL; 3 (4 METHOXYPHENYL) 2 METHYL 4 NITROBUTANAL; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; AMMONIA; IONIC LIQUID; N (2 (DIMETHYLCARBAMOYL)CYCLO HEXYL)BENZAMIDE; NITROOLEFIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 77954348716     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.030     Document Type: Article

References (55)

1. W. Miao, and T.H. Chan Acc. Chem. Res. 39 2006 897 908
2. K. Bica, and P. Gaertner Eur. J. Org. Chem. 2008 3235 3250
3. M.L. Patil, and H. Sasai Chem. Rec. 8 2008 98 108
4. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, and J.-C. Plaquevent Tetrahedron: Asymmetry 14 2003 3081 3093
5. A.D. Headley, and B. Ni Aldrichimica Acta 40 2007 107 117
6. . Toma, M. Meiarová, and R. ebesta Eur. J. Org. Chem. 2009 321 327
7. S. Luo, L. Zhang, and J.-P. Cheng Chem. - Asian J. 4 2009 1184 1195
8. B. Ni, and A.D. Headley Chem. - Eur. J. 16 2010 4426 4436
9. J.J. Jodry, and K. Mikami Tetrahedron Lett. 45 2004 4429 4431
10. V.K. Aggarwal, I. Emme, and A. Mereu Chem. Commun. 2002 1612 1613
11. G. Ebner, S. Schiehser, A. Potthast, and T. Rosenau Tetrahedron Lett. 49 2008 7322 7324
12. J. Dupont, and J. Spencer Angew. Chem., Int. Ed. 43 2004 5296 5297
13. P.S. Kulkarni, L.C. Branco, J.G. Crespo, M.C. Nunes, A. Raymundo, and C.A.M. Afonso Chem. - Eur. J. 13 2007 8478 8488
14. M. Kärnä, M. Lahtinen, and J. Valkonen J. Mol. Struct. 922 2009 64 76
15. P. Wasserscheid, A. Bösmanna, and C. Bolmb Chem. Commun. 2002 200 201
16. P. Juliusz, and F.-K. Joanna Chem. - Eur. J. 11 2005 4441 4449
17. G. Vo Thanh, B. Pegot, and A. Loupy Eur. J. Org. Chem. 2004 1112 1116
18. D.K. Bwambok, H.M. Marwani, V.E. Fernand, S.O. Fakayode, M. Lowry, I. Negulescu, R.M. Strongin, and I.M. Warner Chirality 20 2008 151 158
19. S. Hu, T. Jiang, Z. Zhang, A. Zhu, B. Han, J. Song, Y. Xie, and W. Li Tetrahedron Lett. 48 2007 5613 5617
20. G.-h. Tao, L. He, N. Sun, and Y. Kou Chem. Commun. 2005 3562 3564
21. G.-h. Tao, L. He, W.-s. Liu, L. Xu, W. Xiong, T. Wang, and Y. Kou Green Chem. 8 2006 639 646
22. O. Nguyen Van Buu, A. Aupoix, N. Doan Thi Hong, and G. Vo-Thanh New J. Chem. 33 2009 2060 2072
23. V. Kumar, C. Pei, C.E. Olsen, S.J.C. Schäffer, V.S. Parmar, and S.V. Malhotra Tetrahedron: Asymmetry 19 2008 664 671
24. L. Poletti, C. Chiappe, L. Lay, D. Pieraccini, L. Polito, and G. Russo Green Chem. 9 2007 337 341
25. J. Ding, T. Welton, and D.W. Armstrong Anal. Chem. 76 2004 6819 6822
26. L.M. Yuan, Y. Han, Y. Zhou, X. Meng, Z.Y. Li, M. Zi, and Y.X. Chang Anal. Lett. 39 2006 1439 1449
27. J. Ding, V. Desikan, X. Han, T.L. Xiao, R. Ding, W.S. Jenks, and D.W. Armstrong Org. Lett. 7 2004 335 337
28. B. Pégot, G. Vo-Thanh, D. Gori, and A. Loupy Tetrahedron Lett. 45 2004 6425 6428
29. B. Pégot, O. Nguyen Van Buu, D. Gori, and G. Vo-Thanh Beilstein J. Org. Chem. 2 2006 18 23
30. T.-K.-T. Truong, and G. Vo-Thanh Tetrahedron 2010 10.1016/j.tet.2010.03. 101
31. M. Lombardo, F. Pasi, S. Easwar, and C. Trombini Adv. Synth. Catal. 349 2007 2061 2065
32. Z. Zheng, B.L. Perkins, and B. Ni J. Am. Chem. Soc. 132 2010 50 51
33. Y. Li, X.-Y. Liu, and G. Zhao Tetrahedron: Asymmetry 17 2006 2034 2039
34. Y. Hayashi, H. Gotoh, T. Hayashi, and M. Shoji Angew. Chem., Int. Ed. 44 2005 4212 4215
35. J. Wang, H. Li, B. Lou, L. Zu, H. Guo, and W. Wang Chem. - Eur. J. 12 2006 4321 4332
36. D.-Q. Xu, B.-T. Wang, S.-P. Luo, H.-D. Yue, L.-P. Wang, and Z.-Y. Xu Tetrahedron: Asymmetry 18 2007 1788 1794
37. S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, and J.-P. Cheng Angew. Chem., Int. Ed. 45 2006 3093 3097
38. B. Ni, Q. Zhang, and A.D. Headley Green Chem. 9 2007 737 739
39. Q. Zhang, B. Ni, and A.D. Headley Tetrahedron 64 2008 5091 5097
40. B. Ni, Q. Zhang, K. Dhungana, and A.D. Headley Org. Lett. 11 2009 1037 1040
41. B. Ni, Q. Zhang, and A.D. Headley Tetrahedron Lett. 49 2008 1249 1252
42. X.-B. Wang, K. Kodama, T. Hirose, and G.-Y. Zhang Chin. J. Chem. 28 2010 61 68
43. X.-B. Wang, K. Kodama, T. Hirose, X.-F. Yang, and G.-Y. Zhang Tetrahedron: Asymmetry 21 2010 75 80
44. L.-Y. Wu, Z.-Y. Yan, Y.-X. Xie, Y.-N. Niu, and Y.-M. Liang Tetrahedron: Asymmetry 18 2007 2086 2090
45. C. Chang, S.-H. Li, R.J. Reddy, and K. Chen Adv. Synth. Catal. 351 2009 1273 1278
46. S. Sulzer-Mossé, and A. Alexakis Chem. Commun. 2007 3123 3135
47. J.-T. Liu, and C.-F. Yao Tetrahedron Lett. 42 2001 6147 6150
48. X.-j. Zhang, S.-p. Liu, X.-m. Li, M. Yan, and A.S.C. Chan Chem. Commun. 2009 833 835
49. L.-q. Gu, and G. Zhao Adv. Synth. Catal. 349 2007 1629 1632
50. A. Alexakis, and O. Andrey Org. Lett. 4 2002 3611 3614
51. S. Luo, H. Xu, X. Mi, J. Li, X. Zheng, and J.-P. Cheng J. Org. Chem. 71 2006 9244 9247
52. O. Andrey, A. Alexakis, A. Tomassini, and G. Bernardinelli Adv. Synth. Catal. 346 2004 1147 1168
53. L. Zu, H. Li, J. Wang, X. Yu, and W. Wang Tetrahedron Lett. 47 2006 5131 5134
54. W. Wang, J. Wang, and H. Li Angew. Chem., Int. Ed. 44 2005 1369 1371
55. C. Palomo, S. Vera, A. Mielgo, and E. Gómez-Bengoa Angew. Chem., Int. Ed. 45 2006 5984 5987