Tandem ring-opening/closing reactions of N-Ts aziridines and aryl propargyl alcohols promoted by T-BuOK

Organic Letters

Volumn 11, Issue 5, 2009, Pages 1119-1122

  Wang, Liang ^a,b   Liu, Qi Bin ^a   Wang, Duo Sheng ^a   Li, Xin ^a   Han, Xiu Wen ^a   Xiao, Wen Jing ^b   Zhou, Yong Gui ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIRIDINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OXAZINE DERIVATIVE; PROPANOL; PROPARGYL ALCOHOL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; AZIRIDINES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXAZINES; PROPANOLS;

EID: 64349121534     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802862p     Document Type: Article

References (62)

1. For the recent reviews, see: (a) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. Aziridines and Azirines: Monocyclic. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, UK, 1996; Vol. 1A, p 1.
2. (b) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599.
3. (c) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
4. (d) Hu, X. E. Tetrahedron 2004, 60, 2701.
5. (e) Rayner, C. M. Synlett 1997, 11.
6. (f) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
7. (g) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
8. (h) Kasai, M.; Kono, M. Synlett 1992, 778.
9. (i) Watson, I. D. G.; Yu, L.; Yudin, A. K. Acc. Chem. Res. 2006, 39, 194.
10. (j) Hou, X. L.; Wu, J.; Fan, R. H.; Ding, C. H.; Luo, Z. B.; Dai, L. X. Synlett 2006, 181.
11. For selected recent examples, see: (a) Sun, X.; Ye, S. Q.; Wu, J. Eur. J. Org. Chem. 2006, 4787.
12. (b) Savoia, D.; Alvaro, G.; Fabio, R. D.; Gualandi, A. J. Org. Chem. 2007, 72, 3859.
13. (c) Li, P.; Forbeck, E. M.; Evans, C. D.; Joullié, M. M. Org. Lett. 2006, 8, 5105.
14. (d) Diao, T.; Sun, X.; Fan, R.; Wu, J. Chem. Lett. 2007, 36, 604.
15. (e) Siebert, M. R.; Yudin, A. K.; Tantillo, D. J. Org. Lett. 2008, 10, 57.
16. (f) Wu, J.; Sun, X.; Sun, W. Org. Biomol. Chem. 2006, 4, 4231.
17. (g) Liu, H.; Pattabiraman, V. R.; Vederas, J. C. Org. Lett. 2007, 9, 4211.
18. For selected examples, see: (a) Heinrich, M. R.; Martin, I. P.; Zard, S. Z. Chem. Commun. 2005, 5928.
19. (b) Sureshkumar, D.; Gunasundari, T.; Saravanan, V.; Chandrasekaran, S. Tetrahedron Lett. 2007, 48, 623.
20. (c) Kim, Y.; Ha, H.-J.; Han, K.; Ko, S. W.; Yun, H.; Yoon, J. H.; Min, S. K.; Lee, W. K. Tetrahedron Lett. 2005, 46, 4407.
21. (d) Hou, X.-L.; Fan, R.-H.; Dai, L.-X. J. Org. Chem. 2002, 67, 5295.
22. (e) Sureshkumar, D.; Koutha, S. M.; Chandrasekaran, S. J. Am. Chem. Soc. 2005, 127, 12760.
23. (f) Han, H.; Base, I.; Yoo, E. J.; Lee, J.; Do, Y.; Chang, S. Org. Lett. 2004, 6, 4109.
24. (g) Wu, J.; Sun, X.; Xia, H.-G. Eur. J. Org. Chem. 2005, 4769.
25. (h) Wu, J.; Sun, X.; Li, Y. Eur. J. Org. Chem. 2005, 4271.
26. For reviews, see: (a) Meijere, A. D.; Zezschwitz, P. V.; Bräse, S. Acc. Chem. Res. 2005, 38, 413.
27. (b) Hussain, M. M.; Walsh, P. J. Acc. Chem Res. 2008, 41, 883.
28. (c) Sun, X. L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937.
29. (d) Ajamian, A.; Gleason, J. L. Angew. Chem., Int. Ed. 2004, 43, 3754.
30. (e) Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354.
31. (f) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
32. (g) Enders, D.; Grondal, C.; Huttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
33. (h) Wasike, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
34. (i) Bur, S. K.; Padwa, A. Tetrahedron 2007, 63, 5341.
35. For selected recent examples, see: (a) Ye, L.-W.; Sun, X.-L.; Wang, Q.-G.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 5951.
36. (b) Chen, J.-R.; Li, C.-F.; An, X.-L.; Zhang, J.-J.; Zhu, X.-Y; Xiao, W.-J. Angew. Chem., 0 Int. Ed. 2008, 47, 2489.
37. (c) Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928.
38. (d) Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036.
39. (e) Shi, F.-Q.; Li, Xin.; Xia, Y.; Zhang, L.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 15503.
40. (f) Wang, Q.-G.; Deng, X.-M; Zhu, B.-H.; Ye, L.-W.; Sun, X.-L.; Li, C.-Y.; Zhu, C-Y.; Shen, Q.; Tang, Y. J. Am. Chem. Soc. 2008, 130, 5408.
41. (g) Fan, R.; Wang, W.; Pu, D.; Wu, J. J. Org. Chem. 2007, 72, 5905.
42. (h) Enders, D.; Huttl, M. R. M.; Grondal, C.; Rabbe, G. Nature 2006, 441, 861.
43. (i) Ye, L.-W.; Sun, X.-L.; Zhu, C.-Y.; Tang, Y. Org. Lett. 2006, 8, 3853.
44. (j) Gao, K.; Wu, J. Org. Lett. 2008, 10, 2251.
45. (a) Zhou, Y.-G.; Yang, P.-Y.; Han, X.-W. J. Org. Chem. 2005, 70, 1679.
46. (b) Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357.
47. (c) Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
48. (d) Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2006, 45, 2260.
49. See the Supporting Information.
50. Kundu, N. G.; Chaudhuri, G.; Upadhyay, A. J. Org. Chem. 2001, 66, 20. See the Supporting Information.
51. (a) Tius, M. A.; Hu, H.; Kawakami, J. K.; Petersen, J. B. J. Org. Chem. 1998, 63, 5971.
52. (b) Hu, H.; Smith, D.; Cramer, R. E.; Tius, M. A. J. Am. Chem. Soc. 1999, 121, 9895.
53. For a review see: (a) Wijtmans, R.; Vink, M. K. S.; Schoemaker, H. E.; van Delft, F. L. V.; Blaauw, R. H.; Rutjes, F. P. J. T. Synthesis 2004, 641. For recent examples, see:
54. (b) Yar, M.; Mcgarrigle, E. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2008, 47, 3784.
55. (c) Breuning, M.; Winnacker, M.; Steiner, M. Eur. J. Org. Chem. 2007, 2100.
56. (d) Dhooghe, M.; Vanlangendonck, T.; Tömroos, K. W.; Kimpe, N. D. J. Org. Chem. 2006, 71, 4678.
57. (e) Pedrosa, R.; Andrés, C.; Mendiguchía, P.; Niero, J. J. Ore. Chem. 2006, 71, 8854.
58. (f) Henegar, K. E. J. Org. Chem. 2008, 73 3662.
59. (g) Lanman, B. A.; Myers, A. G. Org. Lett. 2004, 6, 1054.
60. (h) Leijondahl, K.; Borén, L.; Braun, R.; Backvall, J.-E. Org. Lett. 2008, 10, 2027'.
61. (i) Sladojevich, F.; Trabocchi, A.; Guarna, A. Org. Biomol. Chem. 2008, 6, 3328.
62. (j) Zhang, P.; Cedilote, M.; Cleary, T. P.; Pierce, M. E. Tetrahedron Lett. 2007, 48, 8659.