Mitsunobu alkylation of imidazole: A convenient route to chiral ionic liquids

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 631-633

  Kim, Eun Jin ^a   Ko, Soo Y ^a   Dziadulewicz, Edward K ^b  

^a Ewha Womans University   (South Korea)

^b Novatis Inst for Medical Sciences   (United Kingdom)

Author keywords

Chiral ionic liquids; Mitsunobu reaction; N Substituted imidazole

Indexed keywords

IMIDAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; MITSUNOBU REACTION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 11044227129     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.144     Document Type: Article

References (38)

1. T.L. Gilchrist Heterocyclic Chemistry 3rd ed. 1997 Longman Singapore Chapter 8
2. M.R. Grimmett A.R. Katritzky A.J. Boulton Advances in Heterocyclic Chemistry Vol. 27 1980 Academic Press New York
3. For reviews, see: J.S. Wilkes Green Chem. 4 2002 73
4. R. Sheldon Green Chem. 4 2002 73
5. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772
6. T. Welton Chem. Rev. 99 1999 2071
7. Y. Chauvin, and H. Olivier CHEMTECH 1995 26
8. Recent examples: Y. Gu, F. Shi, and Y. Deng J. Org. Chem. 69 2004 391
9. F. Shi, H. Xion, Y. Gu, S. Guo, and Y. Deng Chem. Commun. 2003 1054
10. E.J. Kim, S.Y. Ko, and C.E. Song Helv. Chim. Acta 86 2003 894
11. J.N. Rosa, C.A.M. Afonso, and A.G. Santos Tetrahedron 57 2001 4189
12. T. Tsuchimoto, T. Maeda, E. Shirakawa, and Y. Kawakami Chem. Commun. 2000 1573
13. C.E. Song, W.H. Shim, E.J. Roh, S.-G. Lee, and J.H. Choi Chem. Commun. 2001 1122
14. Recent examples: D. Li, F. Shi, J. Peng, S. Guo, and Y. Deng J. Org. Chem. 69 2004 3582
15. D. Li, F. Shi, S. Guo, and Y. Deng Tetrahedron Lett. 45 2004 265
16. P. Wasserscheid, B. Drießen-Hölscher, R.v. Hal, H.C. Steffens, and J. Zimmermann Chem. Commun. 2003 2038
17. A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes, and J.H. Davis Jr. J. Am. Chem. Soc. 124 2002 5962
18. A.E. Visser, R.P. Swatloski, W.M. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J.H. Davis Jr., and R.D. Rogers Chem. Commun. 2001 135
19. A.S. Larsen, J.D. Holbrey, F.S. Tham, and C.A. Reed J. Am. Chem. Soc. 122 2000 7264
20. T.L. Merrigan, E.D. Bates, S.C. Dorman, and J.H. Davis Jr. Chem. Commun. 2000 2051
21. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, and J.-C. Plaquevent Tetrahedron: Asymmetry 14 2003 3081
22. J. Howarth, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097
23. M.J. Earle, P.B. McCormac, and K.R. Seddon Green Chem. 1999 23
24. P. Wasserscheid, A. Bösmann, and C. Bolm Chem. Commun. 2002 200
25. Y. Ishida, H. Miyauchi, and K. Saigo Chem. Commun. 2002 2240
26. W. Bao, Z. Wang, and Y. Li J. Org. Chem. 68 2003 591
27. J. Levillain, G. Dubant, I. Abrunhosa, M. Gulea, and A.-C. Gaumont Chem. Commun. 2003 2914
28. J. Jodry, and K. Mikami Tetrahedron Lett. 45 2004 4429
29. B. Pégot, G. Vo-Thanh, D. Gori, and A. Loupy Tetrahedron Lett. 45 2004 6425
30. A.A. Gridnev, and I.M. Mihaltseva Synth. Commun. 23 1994 1547
31. S.E. Wolkenberg, D.D. Wisnoski, W.H. Leister, Y. Wang, Z. Zhao, and C.W. Lindsay Org. Lett. 6 2004 1453
32. C. Hardacre, J.D. Holbrey, and S.E.J. McMath Chem. Commun. 22 2001 367
33. There is a literature precedent for the Mitsunobu alkylation of imidazole. See: K.C. Nicolaou, G.-Q. Cao, and J.A. Pfefferkorn Angew. Chem., Int. Ed. 39 2000 739
34. T. Tsunoda, Y. Yamamiya, and S. Itô Tetrahedron Lett. 34 1993 1639
35. T. Tsunoda, Y. Yamamiya, Y. Kawamura, and S. Itô Tetrahedron Lett. 6 1995 2529
36. T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto, and S. Itô Tetrahedron Lett. 37 1996 2463
37. F. Zaragosa, and H. Stephensen J. Org. Chem. 66 2001 2518
38. A. Bombrun, and G. Casi Tetrahedron Lett. 43 2002 2187