Synthesis and application of a recyclable ionic liquid-supported imidazolidinone catalyst in enantioselective 1,3-dipolar cycloaddition

Chemical Communications

Volumn 48, Issue 47, 2012, Pages 5856-5858

  Shen, Zhi Liang ^a   Goh, Kau Kiat Kelvin ^a   Wong, Colin Hong An ^a   Loo, Wan Yi ^a   Yang, Yong Sheng ^a   Lu, Jun ^a   Loh, Teck Peng ^a  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; IMIDAZOLE DERIVATIVE; IMIDAZOLIDINONE; IONIC LIQUID; NITRONE; UNCLASSIFIED DRUG; 2,3 UNSATURATED ALDEHYDE; IMIDAZOLIDINE DERIVATIVE; RECYCLABLE IONIC LIQUID SUPPORTED IMIDAZOLIDINONE;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ENANTIOSELECTIVITY; SOLUBILITY; STEREOCHEMISTRY; SYNTHESIS; CONTROLLED STUDY; PRODUCT RECOVERY; RECYCLING;

EID: 85033415210     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc31830j     Document Type: Article

References (76)

1. A. Berkessel and H. Groger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
2. P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007
3. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed., 2004, 43, 5138
4. B. List, Chem. Commun., 2006 819
5. M. Marigo, K. A. Jogensen, Chem. Commun., 2006 2001
6. A. Dondoni, A. Massi, Angew. Chem. Int. Ed., 2008, 47, 4638
7. X. H. Yu, W. Wang, Org. Biomol. Chem., 2008, 6, 2037
8. L. W. Xu, J. Luo, Y. Lu, Chem. Commun., 2009 1807
9. S. K. Tian, Y. Chen, J. Hang, L. Tang, P. Mcdaid, L. Deng, Acc. Chem. Res., 2004, 37, 621
10. T. Ooi, K. Maruoka, Acc. Chem. Res., 2004, 37, 526
11. B. List, Acc. Chem. Res., 2004, 37, 548
12. W. Notz, F. Tanaka, C. F. Barbas, Acc. Chem. Res., 2004, 37, 580
13. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta, 2006, 39, 79
14. A. Erkkila, I. Majander, P. M. Pihko, Chem. Rev., 2007, 107, 5416
15. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc., 2000, 122, 4243
16. A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc., 2002, 124, 2458
17. R. M. Wilson, W. S. Jen, D. W. C. MacMillan, J. Am. Chem. Soc., 2005, 127, 11616
18. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc., 2000, 122, 9874
19. M. T. Hechavarria Fonseca, B. List, Angew. Chem. Int. Ed., 2004, 43, 3958
20. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc., 2002, 124, 7894
21. S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc., 2003, 125, 1192
22. T. D. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. MacMillan, Science, 2007, 316, 582
23. M. Reiter, S. Torssell, S. Lee, D. W. C. MacMillan, Chem. Sci., 2010, 1, 37
24. R. A. Sheldon, Chem. Commun., 2001 2399
25. C. M. Gordon, Appl. Catal. A, 2001, 222, 101
26. P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed., 2000, 39, 3772
27. J. D. Holbrey, K. R. Seddon, Clean Prod. Processes, 1999, 1, 223
28. T. Welton, Chem. Rev., 1999, 99, 2071
29. H. Zhao, S. V. Malhotra, Aldrichimica Acta, 2002, 35, 75
30. C. E. Song, Chem. Commun., 2004 1033
31. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A. C. Gaumont, J. C. Plaquevent, Tetrahedron: Asymmetry, 2003, 14, 3081
32. J. Dupont, R. F. Souza, P. A. Z. Suarez, Chem. Rev., 2002, 102, 3667
33. S. L. Chen, G. L. Chua, S. J. Ji and T. P. Loh, Ionic liquid: a green solvent for organic transformations I, 2007, ACS Symposium Series, vol. 950 (Ionic Liquids in Organic Synthesis), pp. 161-176
34. S. L. Chen, G. L. Chua, S. J. Ji and T. P. Loh, Ionic liquid: a green solvent for organic transformations II, ACS Symposium Series, vol. 950 (Ionic Liquids in Organic Synthesis), 2007, pp. 177-193
35. S. Z. Luo, L. Zhang, J. P. Cheng, Chem.-Asian J., 2009, 4, 1184
36. A. Winkel, P. V. G. Reddy, R. Wilhelm, Synlett, 2008 999
37. K. Bica, P. Gaertner, Eur. J. Org. Chem., 2008 3235
38. W. S. Miao, T. H. Chan, Acc. Chem. Res., 2006, 39, 897
39. X. W. Chen, X. H. Li, A. X. Hu, F. R. Wang, Tetrahedron: Asymmetry, 2008, 19, 1
40. S.-g. Lee, Chem. Commun., 2006 1049
41. C. Baudequin, D. Bregeon, J. Levillain, F. Guillen, J. C. Plaquevent, A. C. Gaumont, Tetrahedron: Asymmetry, 2005, 16, 3921
42. J. Ding, D. W. Armstrong, Chirality, 2005, 17, 281
43. P. Dominguez de Maria, Angew. Chem. Int. Ed., 2008, 47, 6960
44. A. F. Trindade, P. M. P. Gois, C. A. M. Afonso, Chem. Rev., 2009, 109, 418
45. R. Šebesta, I. Kmentová, Š. Toma, Green Chem., 2008, 10, 484
46. S. Z. Luo, X. L. Mi, L. Zhang, S. Liu, H. Xu, J. P. Cheng, Angew. Chem. Int. Ed., 2006, 45, 3093
47. W. S. Miao, T. H. Chan, Adv. Synth. Catal., 2006, 348, 1711
48. S. Z. Luo, L. Zhang, X. L. Mi, Y. P. Qiao, J. P. Cheng, J. Org. Chem., 2007, 72, 9350
49. N. Audic, H. Clavier, M. Mauduit, J. C. Guillemin, J. Am. Chem. Soc., 2003, 125, 9248
50. T. J. Geldbach, P. J. Dyson, J. Am. Chem. Soc., 2004, 126, 8114
51. W. X. Qian, E. L. Jin, W. L. Bao, Y. M. Zhang, Angew. Chem. Int. Ed., 2005, 44, 952
52. L. Zhang, L. Y. Cui, X. Li, J. Y. Li, S. Z. Luo, J. P. Cheng, Chem.-Eur. J., 2010, 16, 2045
53. M. Lombardo, M. Chiarucci, C. Trombini, Chem.-Eur. J., 2008, 14, 11288
54. H. Hagiwara, T. Kuroda, T. Hoshi, T. Suzuki, Adv. Synth. Catal., 2010, 352, 909
55. T. P. Loh, L. C. Feng, H. Y. Yang, J. Y. Yang, Tetrahedron Lett., 2002, 43, 8741
56. S. L. Chen, S. J. Ji, T. P. Loh, Tetrahedron Lett., 2003, 44, 2405
57. J. Lu, S. J. Ji, R. Qian, J. P. Chen, Y. Liu, T. P. Loh, Synlett, 2004 534
58. Z. L. Shen, W. J. Zhou, Y. T. Liu, S. J. Ji, T. P. Loh, Green Chem., 2008, 10, 283
59. S. L. Chen, S. J. Ji, T. P. Loh, Tetrahedron Lett., 2004, 45, 375
60. Z. L. Shen, S. J. Ji, T. P. Loh, Tetrahedron Lett., 2005, 46, 3137
61. J. Lu, S. J. Ji, T. P. Loh, Chem. Commun., 2005 2345
62. F. Fu, Y. C. Teo, T. P. Loh, Org. Lett., 2006, 8, 5999
63. J. F. Zhao, B. H. Tan, M. K. Zhu, T. B. W. Tjan, T. P. Loh, Adv. Synth. Catal., 2010, 352, 2085
64. J. J. Tufariello, in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, John Wiley and Sons, Chichester, 1984, vol. 2, p. 83
65. K. B. G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, Wiley-VCH, Weinheim, 1988
66. K. V. Gothelf, K. A. Jørgensen, Chem. Rev., 1998, 98, 863
67. R. Huisgen, Angew. Chem. Int. Ed., 1963, 2, 565
68. K. V. Gothelf and K. A. Jorgensen, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, ed. A. Padwa, Wiley, New York, 2002
69. K. V. Gothelf, in Cycloaddition Reactions in Organic Synthesis, ed. S. Kobayashi and K. A. Jorgensen, Wiley-VCH, Weinheim, 2002, pp. 211-247
70. S. Karlsson, H.-E. Hogberg, Tetrahedron: Asymmetry, 2002, 13, 923
71. S. Karlsson, H.-E. Hogberg, Eur. J. Org. Chem., 2003 2782
72. S. S. Chow, M. Nevalainen, C. A. Evans, C. W. Johannes, Tetrahedron Lett., 2007, 48, 277
73. M. Lemay, J. Trant, W. W. Ogilvie, Tetrahedron, 2007, 63, 11644
74. L. Weselinski, P. Stepniak, J. Jurczak, Synlett, 2009 2261
75. A. Puglisi, M. Benaglia, M. Cinquini, F. Cozzi, G. Celentano, Eur. J. Org. Chem., 2004 567
76. M. Frederickson, Tetrahedron, 1997, 53, 403