Gold-catalyzed addition of N-hydroxy heterocycles to alkynes and subsequent 3,3-sigmatropic rearrangement

Organic Letters

Volumn 15, Issue 4, 2013, Pages 724-727

  Kumar, Manish ^a   Scobie, Martin ^b   Mashuta, Mark S ^a   Hammond, Gerald B ^a   Xu, Bo ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZOTRIAZOLE; GOLD; TRIAZOLE DERIVATIVE; VINYL DERIVATIVE; VINYL ETHER;

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

ALKYNES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; GOLD; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIAZOLES; VINYL COMPOUNDS;

EID: 84873977254     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4000789     Document Type: Article

References (31)

1. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232-5241
2. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994-2009
3. Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766-1775
4. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378
5. Widenhoefer, R. A. Chem.-Eur. J. 2008, 14, 5382-5391
6. Muzart, J. Tetrahedron 2008, 64, 5815-5849
7. Zhang, C.; De, C. K.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 416-7
8. Trost, B. M.; Maulide, N.; Livingston, R. C. J. Am. Chem. Soc. 2008, 16502-16503
9. Fustero, S.; Moscardo, J.; Jimenez, D.; Perez-Carrion, M. D.; Sanchez-Rosello, M.; Del Pozo, C. Chemistry 2008, 14, 9868-72
10. Wu, W.; Su, W. J. Am. Chem. Soc. 2011, 133, 11924-11927
11. Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226-7236
12. Ye, L.; Cui, L.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258-3259
13. Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550-8551
14. Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070-14072
15. He, W.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2011, 133, 8482-8485
16. Cui, L.; Zhang, G.; Peng, Y.; Zhang, L. Org. Lett. 2009, 11, 1225-1228
17. Luo, Y.; Zhang, G.; Hwang, E. S.; Wilcoxon, T. A.; Zhang, L. Beilstein J. Org. Chem. 2011, 7, 596-600
18. Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160-4161
19. Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156-5159
20. Fang, R.; Yang, L. Organometallics 2012, 31, 3043-3055
21. Cuenca, A. B.; Montserrat, S.; Hossain, K. M.; Mancha, G.; Lledós, A.; Medio-Simón, M.; Ujaque, G.; Asensio, G. Org. Lett. 2009, 11, 4906-4909
22. Wang, Y.; Ye, L.; Zhang, L. Chem. Commun. 2011, 47, 7815-7817
23. Wang, Y.; Liu, L.; Zhang, L. Chem. Sci. 2013, 4, 739-746
24. Lehmann, F.; Koolmeister, T.; Odell, L. R.; Scobie, M. Org. Lett. 2009, 11, 5078-5081
25. Loudon, J. D.; Tennant, G. Q. Rev., Chem. Soc. 1964, 18, 389-413
26. Spence, T. W. M.; Tennant, G. J. Chem. Soc., Perkin Trans. 1 1972, 0, 97-102
27. Wang, W.; Jasinski, J.; Hammond, G. B.; Xu, B. Angew. Chem., Int. Ed. 2010, 49, 7247-7252
28. Guo, Y.; Twamley, B.; Shreeve, J. n. M. Org. Biomol. Chem. 2009, 7, 1716-1722
29. Kim, K.-Y.; Kim, B. C.; Lee, H. B.; Shin, H. J. Org. Chem. 2008, 73, 8106-8108
30. Prakash, G. K. S.; Beier, P. Angew. Chem., Int. Ed. 2006, 45, 2172-2174
31. de Haro, T.; Nevado, C. Adv. Synth. Catal. 2010, 352, 2767-2772