Silver-catalyzed exo-dig-azacyclization/[3+2] cycloaddition cascades on 1-tosylhydrazon-4-oxy-5-yne Substrates: Applicability to Diverse Alkenes

Advanced Synthesis and Catalysis

Volumn 353, Issue 11-12, 2011, Pages 1877-1882

  Huple, Deepak B ^a   Chen, Chun Hao ^a   Das, Arindam ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

6 exo dig azacyclization; 3+2 cycloaddition; azacyclic synthesis; cascade reactions; silver catalysis

Indexed keywords

EID: 80051967772     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100263     Document Type: Article

References (44)

1. Reviews on gold-catalyzed annulation or cycloaddition reactions, see
2. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395
3. N. T. Patil, Y. Yamamoto, ARKIVOC 2007, 5, 6
4. S. Md. Abu Sohel, R.-S. Liu, Chem. Soc. Rev. 2009, 38, 2269
5. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478
6. Angew. Chem. Int. Ed. 2007, 46, 3410
7. N. D. Shapiro, F. D. Toste, Synlett 2010, 675.
8. Selected examples for Au- and Pt-catalyzed cyclization/cycloaddition cascades, see
9. C.-C. Lin, T.-M. Teng, C. C. Tsai, H.-Y. Liao, R.-S. Liu, J. Am. Chem. Soc. 2008, 130, 16417
10. T. M. Teng, M. S. Lin, D. Vasu, S. Bhunia, T.-A. Liu, R.-S. Liu, Chem. Eur. J. 2010, 16, 4744
11. H.-S. Yeom, J.-E. Lee, S. Shin, Angew. Chem. 2008, 120, 7148
12. Angew. Chem. Int. Ed. 2008, 47, 7040
13. G. Zhang, X. Huang, G. Li, L. Zhang, J. Am. Chem. Soc. 2008, 130, 1814
14. F. Liu, Y. Yu, J. Zhang, Angew. Chem. 2009, 121, 5613
15. Angew. Chem. Int. Ed. 2009, 48, 5505
16. N. D. Shapiro, Y. Shi, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 11654
17. N. D. Shapiro, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 9244.
18. For the [4+3] cycloaddition of s-cis-oxonium ions B, see selected examples
19. N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. 2003, 115, 3628
20. Angew. Chem. Int. Ed. 2003, 42, 3504
21. N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458
22. Y.-C. Hsu, C.-M. Ting, R.-S. Liu, J. Am. Chem. Soc. 2009, 131, 2090
23. X.-Z. Shu, S.-C. Zhao, K.-G. Ji, Z.-J. Zheng, X.-Y. Liu, Y.-M. Liang, Eur. J. Org. Chem. 2009, 117.
24. For the [3+2] cycloaddition of s-cis-oxonium ions B, see selected examples
25. H. Kusama, K. Ishida, H. Funami, N. Iwasawa, Angew. Chem. 2008, 120, 4981
26. Angew. Chem. Int. Ed. 2008, 47, 4903
27. G. Li, X. Huang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 6944
28. C. H. Oh, J. H. Lee, S. J. Lee, J. I. Kim, C. S. Hong, Angew. Chem. 2008, 120, 7615
29. Angew. Chem. Int. Ed. 2008, 47, 7505
30. C. H. Oh, S. M. Lee, C. S. Hong, Org. Lett. 2010, 12, 1308.
31. T.-M. Teng, A. Das, D. B. Huple, R.-S. Liu, J. Am. Chem. Soc. 2010, 132, 12565.
32. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, (Eds.:, A. Padwa, W. H. Pearson,), John Wiley and Sons. Hoboken, NJ, 2003
33. S. Kanemasa, Synlett 2002, 1371
34. C. Najera, J. M. Sansano, Curr. Org. Chem. 2003, 7, 1105.
35. For metal-catalyzed [3+2] dipolar cycloadditions, see selected reviews
36. L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887
37. K. V. Gothelf, K. A. Jogensen, Chem. Rev. 1998, 98, 863
38. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395.
39. S. Ye, X. Yang, J. Wu, Chem. Commun. 2010, 46, 5238.
40. [9b] and enones; these reactions are distinct from our work; see
41. Z. Chen, X. Yang, J. Wu, Chem. Commun. 2009, 3469
42. X. Yu, S. Ye, J. Wu, Adv. Synth. Catal. 2010, 352, 2050
43. Z. Chen, J. Wu, Org. Lett. 2010, 12, 4856.
44. 2Me rather than the expected oxidation step