N-Heterocyclic carbene: a highly efficient catalyst in the reactions of aziridines with silylated nucleophiles

Tetrahedron Letters

Volumn 47, Issue 28, 2006, Pages 4813-4816

  Wu, Jie ^a,b   Sun, Xiaoyu ^a   Ye, Shengqing ^a   Sun, Wei ^a  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; CARBENOID;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; SILYLATION; SYNTHESIS;

EID: 33744794614     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.048     Document Type: Article

References (70)

1. For examples, see:. Herrmann W.A., Ofele K., von Preysing D., and Schneider S.K. J. Organomet. Chem. 687 (2003) 229
2. Yong B.S., and Nolan S.P. Chemtracts 16 (2003) 205
3. Navarro O., Kelly III R.A., and Nolan S.P. J. Am. Chem. Soc. 125 (2003) 16194
4. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176
5. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
6. Kremzow D., Seidel G., Lehmann C.W., and Fürstner A. Chem. Eur. J. 11 (2005) 1833
7. Nair V., Bindu S., Sreekumar V., and Rath N.P. Org. Lett. 5 (2003) 665
8. Nair V., Bindu S., and Sreekumar V. Angew. Chem., Int. Ed. 43 (2004) 5130
9. Fei Z.-F., Zhao D.-B., Geldbach T.J., Scopelliti R., and Dyson P.J. Chem. Eur. J. 10 (2004) 4886
10. Nair V., Sreekumar V., Bindu S., and Suresh E. Org. Lett. 7 (2005) 2297
11. Rigby J.H., and Wang Z.Q. Org. Lett. 4 (2002) 4289
12. For reviews, see: Wu, J.; Sun, X. Chin. J. Org. Chem., in press.
13. Nair V., Bindu S., and Sreekumar V. Angew. Chem., Int. Ed. 43 (2004) 5130
14. Suzuki Y., Toyota T., Imada F., Sato M., and Miyashita A. Chem. Commun. (2003) 1314
15. Miyashita A., Suzuki Y., Iwamoto K.-I., Oishi E., and Higashino T. Heterocycles 49 (1998) 405
16. Miyashita A., Suzuki Y., Iwamoto K.-I., and Higashino T. Chem. Pharm. Bull. 46 (1998) 390
17. For recent examples, see:. Raghavan S., and Anuradha K. Tetrahedron Lett. 43 (2002) 5181
18. Sohn S.S., Rosen E.L., and Bode J.W. J. Am. Chem. Soc. 126 (2004) 14370
19. Kerr M.S., Alaniz J., and Rovis T. J. Am. Chem. Soc. 124 (2002) 10298
20. Kerr M.S., and Rovis T. Synlett (2003) 1934
21. Kerr M.S., and Rovis T. J. Am. Chem. Soc. 126 (2004) 8876
22. Readde Alaniz J., and Rovis T. J. Am. Chem. Soc. 127 (2005) 6284
23. Nakamura T., Hara O., Tamura T., Makino K., and Hamada Y. Synlett 1 (2004) 155
24. Mennen S.M., Gipson J.D., Kim Y.R., and Miller S.J. J. Am. Chem. Soc. 127 (2005) 1654
25. Mattson A.E., Bharadwaj A.R., and Scheidt K.A. J. Am. Chem. Soc. 126 (2004) 2314
26. Bharadwaj A.R., and Scheidt K.A. Org. Lett. 14 (2004) 2465
27. Harrington P.E., and Tius M.A. Org. Lett. 1 (1999) 649
28. Murry J.A., Frantz D.E., Soheili A., Tillyer R., Grabowski E.J.J., and Reider P.J. J. Am. Chem. Soc. 123 (2001) 9696
29. Mattson A.E., and Scheidt K.A. Org. Lett. 6 (2004) 4363
30. Burstein C., and Glorius R. Angew. Chem., Int. Ed. 43 (2004) 6205
31. Pohl M., Lingen B., and Müller M. Chem. Eur. J. 8 (2002) 5288
32. Hachisu Y., Bode J.W., and Suzuki K. J. Am. Chem. Soc. 125 (2003) 8432
33. Johnson J.S. Angew. Chem., Int. Ed. 43 (2004) 1326
34. Enders D., and Niemeier O. Synlett (2004) 2111
35. Song J.J., Tan Z., Reeves J.T., Gallou F., Yee N.K., and Senanayake C.H. Org. Lett. 7 (2005) 2193
36. Grasa G.A., Kissling R.M., and Nolan S.P. Org. Lett. 4 (2002) 3583
37. Grasa G.A., Güveli T., Singh R., and Nolan S.P. J. Org. Chem. 68 (2003) 2812
38. Nyce G.W., Lamboy J.A., Connor E.F., Waymouth R.M., and Hedrick J.L. Org. Lett. 4 (2002) 3587
39. Singh R., Kissling R.M., Letellier M.-A., and Nolan S.P. J. Org. Chem. 69 (2004) 209
40. Suzuki Y., Yamauchi K., Muramatsu K., and Sato M. Chem. Commun. (2004) 2770
41. Duong H.A., Cross M.J., and Louie J. Org. Lett. 6 (2004) 4679
42. For reviews of syntheses and reactions of activated and unactivated aziridines see:. Pawda A., Pearson W.H., Lian B.W., and Bergmeier S.C. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 1a (1996), Pergamon, New York
43. Pawda A., and Woolhouse A.D. In: Lwowski W. (Ed). Comprehensive Heterocyclic Chemistry Vol. 7 (1984), Pergamon, Oxford, UK
44. Tanner D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599
45. Ibuka T. Chem. Soc. Rev. 27 (1998) 145
46. Li A.-H., Dai L.-X., and Aggarwal V.K. Chem. Rev. 97 (1997) 2341
47. Stamm H. J. Prakt. Chem. (1999) 319
48. Hu X.E. Tetrahedron 60 (2004) 2701
49. Ma L.G., and Xu J.X. Prog. Chem. 16 (2004) 220
50. Rayner C.M. Synlett (1997) 11
51. McCoull W., and Davis F.A. Synthesis (2000) 1347
52. Sweeney J.B. Chem. Soc. Rev. 31 (2002) 247
53. Dhanukar V.H., and Zavialov L.A. Curr. Opin. Drug Discovery Dev. 5 (2002) 918
54. Hou X.L., Wu J., Fan R.H., Ding C.H., Luo Z.B., and Dai L.X. Synlett (2006) 181
55. For examples of the reaction of aziridine with silyl nucleophiles, see:. Matsubara S., Kodama T., and Utimoto K. Tetrahedron Lett. 31 (1990) 6379
56. Leung W.H., Yu M.T., Wu M.C., and Yeung L.L. Tetrahedron Lett. 37 (1996) 891
57. Ferraris D., Drury III W.J., Cox C., and Lectka J. J. Org. Chem. 63 (1998) 4568
58. Li Z., Fernandez M., and Jacobsen E.N. Org. Lett. 1 (1999) 1611
59. Chandrasekhar M., Sekar G., and Singh V.K. Tetrahedron Lett. 31 (1990) 6379
60. Shin S.-H., Han E.Y., Park C.S., Lee W.K., and Ha H.-J. Tetrahedron: Asymmetry 11 (2000) 3293
61. Yadav J.S., Reddy B.V.S., Kumar G.M., and Murthy C.V.S.R. Synth. Commun. 32 (2000) 1797
62. Reddy M.A., Reddy L.R., Bhanumathi N., and Rao K.R. Chem. Lett. (2001) 246
63. Osborn H.M.I., and Sweeney J.B. Synlett (1994) 145
64. Chandrasekhar M., Sekar G., and Singh V.K. Tetrahedron Lett. 41 (2000) 10079
65. Wu J., Hou X.-L., and Dai L.-X. J. Org. Chem. 65 (2000) 1344
66. Wu J., Sun X., and Xia H.-G. Eur. J. Org. Chem. (2005) 4769
67. Minakata S., Okada Y., Oderaotoshi Y., and Komatsu M. Org. Lett. 7 (2005) 3509
68. A review on pentacoordinated silicon chemistry:. Chuit C.C., Corriu R.J., Reye C., and Young J.C. Chem. Rev. 93 (1993) 1371
69. Sakurai H. Synlett (1989) 1
70. 3) δ (ppm): 1.26-1.32 (m, 3H), 1.61-1.71 (m, 3H), 2.16-2.27 (m, 2H), 2.43 (s, 3H), 3.24-3.27 (m, 1H), 3.99-4.01 (m, 1H), 5.01-5.02 (d, J 6.2 Hz, 1H), 7.26-7.31 (m, 2H), 7.8 (d, J 8.3 Hz, 2H).