Sulfur-assisted Propargyl-Allenyl isomerizations and electrocyclizations for the convenient and efficient synthesis of polyfunctionalized benzenes and naphthalenes

Organic Letters

Volumn 12, Issue 16, 2010, Pages 3674-3677

  Zhou, Hongwei ^a   Xing, Yanpeng ^a   Yao, Jinzhong ^a   Chen, Junhui ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77955679627     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101479d     Document Type: Article

References (29)

1. Nakamura, I.; Zhang, D.; Terada, M. J. Am. Chem. Soc. 2010, 132, 7884
2. Cabaleiro-Lago, E. M.; Rodriguez-Otero, J.; Garcia-Lopez, R. M.; Pena-Gallego, A.; Hermida-Ramon, J. M. Chem.-Eur. J. 2005, 11, 5966
3. Lopez, C. S.; Faza, O. N.; Cossio, F. P.; York, D. M.; de Lera, A. R. Chem.-Eur. J. 2005, 11, 1734
4. Wang, F.; Tong, X.; Cheng, J.; Zhang, Z. Chem.-Eur. J. 2004, 10, 5338
5. Rodriguez-Otero, J.; Cabaleiro-Lago, E. M. Angew. Chem., Int. Ed. 2002, 41, 1147
6. Myers, A. G.; Dragovicb, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369
7. Porter, N. A.; Hogenkamp, D. J.; Khouri, F. F. J. Am. Chem. Soc. 1990, 112, 2403
8. Zhou, H.; Xie, Y.; Ren, L.; Wang, K. Adv. Synth. Catal. 2009, 351, 1289
9. Zhou, H.; Xie, Y.; Ren, L.; Su, R. Org. Lett. 2010, 12, 356
10. Zhou, H.; Zhu, D.; Xie, Y.; Huang, H.; Wang, K. J. Org. Chem. 2010, 75, 2706
11. Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440
12. Sromek, A. W.; Gevorgyan, V. Top. Curr. Chem. 2007, 274, 77
13. Zafrani, Y.; Gottlieb, H. E.; Sprecher, M.; Braverman, S. J. Org. Chem. 2005, 70, 10166
14. Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2003, 42, 98
15. Zafrani, Y.; Cherkinsky, M.; Gottlieb, H. E.; Braverman, S. Tetrahedron 2003, 59, 2641
16. Braverman, S.; Cherkinsky, M.; Birsa, M. L.; Zafrani, Y. Eur. J. Org. Chem. 2002, 18, 3198
17. Braverman, S.; Zafrani, Y.; Gottlieb, H. E. Tetrahedron 2001, 57, 9177
18. Garratt, P. J.; Neoh, S. B. J. Am. Chem. Soc. 1975, 97, 3255
19. For the detailed processes, see the Supporting Information.
20. Barry, N.; Brondel, N.; Lawrence, S. E.; Maguire, A. R. Tetrahedron 2009, 65, 10660
21. Yusubov, M. S.; Yusubova, R. Y.; Funk, T. V.; Chi, K. W.; Zhdankin, V. V. Synthesis 2009, 15, 2505
22. Nakamura, S.; Nakagawa, R.; Watanabe, Y.; Toru, T. J. Am. Chem. Soc. 2000, 122, 11340
23. Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1979, 44, 713
24. Yu, Z.; Verkade, J. G. Tetrahedron Lett. 1998, 39, 2671
25. Gutierrez, C. G.; Summerhays, L. R. J. Org. Chem. 1984, 49, 5206
26. Rasool, N.; Rashid, M. A.; Reinke, H.; Fischerb, C.; Langer, P. Tetrahedron 2007, 63, 11626
27. Sato, T.; Okazaki, H.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1988, 110, 5209
28. Arroyo, Y.; Rodri g;uez, J. F.; Santos, M.; Tejedor; Ruano, J. L. G. J. Org. Chem. 2007, 72, 1035
29. Harada, T.; Morimoto, M.; Nagasawa, M.; Takamura, N.; Inoue, H.; Ohishi, T.; Takeda, M. Chem. Pharm. Bull. 1992, 40, 1986