Synthesis of novel chiral imidazolium-based ionic liquids derived from isosorbide and their applications in asymmetric aza Diels-Alder reaction

Tetrahedron

Volumn 65, Issue 11, 2009, Pages 2260-2265

  Nguyen Van Buu, Olivier ^a   Aupoix, Audrey ^a   Vo Thanh, Giang ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; ISOSORBIDE;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

ALNUS;

EID: 59749098452     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.055     Document Type: Article

References (79)

1. Welton T. Chem. Rev. (1999) 2071
2. Wasserscheid P., and Keim W. Angew. Chem., Int. Ed. 39 (2000) 3772
3. Hagiwara R., and Ito Y. J. Fluorine Chem. 105 (2000) 221
4. Rogers R.D., and Seddon K.R. Ionic Liquids Industrial Applications to Green Chemistry. ACS Symposium Series Vol. 818 (2001)
5. Wasserscheid P., and Welton T. Ionic Liquids in Synthesis (2002), Wiley-VCH, Weinheim
6. Dupont J., de Souza R.F., and Suarez P.A.Z. Chem. Rev. 102 (2002) 3667
7. Sheldon R.A. Green Chem. (2005) 267
8. Ding J., and Armstrong D.W. Chirality 17 (2005) 281
9. Baudequin C., Brégeon D., Levillain J., Guillen F., Plaquevent J.-C., and Gaumont A.-C. Tetrahedron: Asymmetry 16 (2005) 3921
10. Chen X., Li X., Hu A., and Wang F. Tetrahedron: Asymmetry 19 (2008) 1
11. Bica K., and Gaertner P. Eur. J. Org. Chem. (2008) 3235
12. Pégot B., Vo-Thanh G., Gori D., and Loupy A. Tetrahedron Lett. 45 (2004) 6425
13. Ding J., Desikan V., Han X., Xiao T.L., Ding R., Jenks W.S., and Armtrong D.W. Org. Lett. 7 (2005) 335
14. Wang Z., Wang Q., Zhang Y., and Bao W. Tetrahedron Lett. 46 (2005) 4657
15. Luo S., Mi X., Zhang L., Liu S., Xu H., and Cheng J.-P. Angew. Chem., Int. Ed. 45 (2006) 3093
16. Gausepohl R., Buskens P., Kleinen J., Bruckmann A., Lehmann C.W., Klankermayer J., and Leitner W. Angew. Chem., Int. Ed. 45 (2006) 3689
17. Branco L.C., Gois P.M.P., Lourenço N.M.T., Kurteva V.B., and Afonso C.A.M. Chem. Commun. (2006) 2371
18. Malhotra S.V., and Wang Y. Tetrahedron: Asymmetry 17 (2006) 1032
19. Pádár P., Bokros A., Paragi G., Forgó P., Kele Z., Howarth N.M., and Kovács L. J. Org. Chem. (2006) 8669
20. Pégot B., Nguyen Van Buu O., Gori D., and Vo-Thanh G. Beilstein J. Org. Chem. 2 (2006) 18
21. Zhou L., and Wang L. Chem. Lett. 36 (2007) 628
22. Ni B., Zhang Q., and Headley A.D. Green Chem. 9 (2007) 737
23. Nguyen Van Buu O., and Vo-Thanh G. Lett. Org. Chem. 4 (2007) 158
24. Yadav L.D.S., Rai A., Rai V., and Awasthi C. Tetrahedron 64 (2008) 1420
25. Zhou W., Xu L.W., Qiu H.Y., Lai G.Q., Xia C.G., and Jiang J.X. Helv. Chim. Acta 91 (2008) 53
26. Biedtron T., and Kubisa P. Polym. Int. 52 (2003) 1584
27. Ma H.-Y., Wan X.-H., Chen X.-F., and Zhou Q.F. Chin. J. Polym. Sci. 21 (2003) 265
28. Biedtron T., and Kubisa P. J. Polym. Sci., Part A: Polym. Chem. 43 (2005) 3454
29. Ding J., Welton T., and Armstrong D.W. Anal. Chem. 76 (2004) 6819
30. Rizvi S.A.A., and Shamsi S.A. Anal. Chem. 78 (2006) 7061
31. Tosoni M., Laschat S., and Baro A. Helv. Chim. Acta 87 (2004) 2742
32. Baudoux J., Judeinstein P., Cahard D., and Plaquevent J.-C. Tetrahedron Lett. 46 (2005) 1137
33. Wasserscheid P., Bosmann A., and Bolm C. Chem. Commun. (2002) 200
34. Ishida Y., Miyauchi H., and Saigo K. Chem. Commun. (2002) 2240
35. Levillain J., Dubant G., Abrunhosa I., Gulea M., and Gaumont A.-C. Chem. Commun. (2003) 2914
36. Clavier H., Boulanger L., Audic N., Toupet L., Mauduit M., and Guillemin J.-C. Chem. Commun. (2004) 1224
37. Ishida Y., Sasaki D., Miyauchi H., and Saigo K. Tetrahedron 45 (2004) 9455
38. Jurcik V., and Wilhelm R. Tetrahedron: Asymmetry 17 (2006) 801
39. Kagan H.B., and Riant O. Chem. Rev. 92 (1992) 1007
40. Sheldon R.A. Chirotechnology: Industrial Synthesis of Optically Active Compounds (1993), Marcel Dekker, New York, NY p 145
41. Krantz J.C., Carr C.J., Forman S.E., and Ellis F.W. J. Pharmacol. 67 (1939) 191
42. Wang J., Xu M.H., Zhong M., and Lin G. Chin. Chem. Lett. 9 (1998) 325
43. Xu M.H., Lin H.M., Xia Q.G., and Jun L. Chin. J. Chem. 16 (1998) 561
44. Loupy A., and Monteux D. Tetrahedron Lett. 37 (1996) 7023
45. Carcedo C., Dervisi A., Fallis A.I., Ooi L., and Malik A.K.M. Chem. Commun. (2004) 1236
46. Kumar V., Olsen C.E., Schaffer S.J.C., Parmar V.S., and Malhotra S.V. Org. Lett. 9 (2007) 3905
47. Kumar V., Pei C., Olsen C.E., Schaffer S.J.C., Parmar V.S., and Malhotra S.V. Tetrahedron: Asymmetry 19 (2008) 664
48. Vo-Thanh G., Pégot B., and Loupy A. Eur. J. Org. Chem. (2004) 1112
49. Cekovik Z., and Tokic Z. Synthesis (1989) 610
50. Abenhaim D., Loupy A., Munnier L., Tamion R., Marsais F., and Quéguiner G. Carbohydr. Res. 261 (1994) 255
51. Tamion R., Marsais F., Ribereau P., Queguiner G., Abenhaim D., Loupy A., and Munnier L. Tetrahedron: Asymmetry 4 (1993) 1879
52. Kuma S., and Ramachandra U. Tetrahedron 61 (2005) 4141
53. Varma R.S., and Namboodiri V.V. Chem. Commun. (2001) 643
54. Varma R.S., and Namboodiri V.V. Pure Appl. Chem. 73 (2001) 1309
55. Khadilkar B.M., and Rebeiro G.L. Org. Process Res. Dev. 6 (2002) 826
56. Law M.C., Wong K.Y., and Chan T.H. Green Chem. 4 (2002) 328
57. Varma R.S., and Namboodiri V.V. Chem. Commun. (2002) 342
58. Dubreuil J.F., Famelart M.H., and Bazureau J.P. Org. Process Res. Dev. 6 (2002) 374
59. Varma R.S., and Namboodiri V.V. Tetrahedron Lett. 43 (2002) 5381
60. Deetlefs M., and Seddon K.S. Green Chem. 5 (2003) 181
61. Lévêque J.M., Estager J., Draye M., Boffa L., Cravotto G., and Bonrath W. Monatsh. Chem. 138 (2007) 1103
62. Cravotto G., Calcio-Gaudino E., Boffa L., Lévêque J.M., Estager J., and Bonrath W. Molecules 13 (2008) 149
63. For recent reviews on microwave chemistry, see:
64. De la Hoz A., Diaz-Ortis A., Moreno A., and Langa F. Eur. J. Org. Chem. (2000) 3659
65. Alterman M., and Hallberg A. J. Org. Chem. 65 (2000) 7984
66. Perreux L., and Loupy A. Tetrahedron 57 (2001) 9199
67. Lidström P., Tierney J., Wathey P., and Westman J. Tetrahedron 57 (2001) 9225
68. Hayes B.L. Microwave Synthesis: Chemistry at the Speed of Light (2002), CEM, Matthews, NC
69. Loupy A. Microwaves in Organic Synthesis (2006), Wiley-VCH, Weinheim
70. Kappe C.O., and Stadler A. Microwaves in Organic and Medicinal Chemistry (2005), Wiley-VCH, Weinheim
71. Polshettiwar V., and Varma R.S. Acc. Chem. Res. 41 (2008) 629
72. Stoss P., Merrath P., and Schluter G. Synthesis (1987) 174
73. Pégot B., and Vo-Thanh G. Synlett (2005) 1409
74. Hattori K., and Yamamoto H. Tetrahedron 49 (1993) 1749
75. Ballcells J., Colonna S., and Fornasier R. Synthesis (1976) 266
76. Colonna S., and Fornasier R. J. Chem. Soc., Perkin Trans. 1 (1978) 371
77. Fischer T., Sethi A., Welton T., and Woolf J. Tetrahedron Lett. 40 (1999) 793
78. Zulfiqar F., and Kitazume T. Green Chem. 2 (2000) 137
79. Loncaric C., Manabe K., and Kobayashi S. Chem. Commun. (2003) 574