Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans

Organic Letters

Volumn 8, Issue 4, 2006, Pages 573-576

  Bowman, Roy K ^a   Johnson, Jeffrey S ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644778567     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052700k     Document Type: Article

References (24)

1. (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
2. (b) Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240-3241.
3. (c) Risatti, C. A.; Taylor, R. E. Angew. Chem., Int. Ed. 2004, 43, 6671-6672.
4. (d) Papageorgiou, C. D.; de Dios, M. A. C.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 4641-4644.
5. (e) Liao, W.-W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 125, 13030-13031.
6. (a) Wenkert, E.; Alonso, M. E.; Buckwalter, B. L.; Chou, K. J. J. Am. Chem. Soc. 1977, 99, 4778-4782.
7. (b) Davies, H. M. L.; Ahmed, G.; Calvo, R. L.; Churchill, M. R.; Churchill, D. G. J. Org. Chem. 1998, 63, 2641-2645.
8. (c) Yadav, V. K.; Balamurugan, R. Org. Lett. 2001, 3, 2717-2719.
9. Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc. 2004, 126, 9645-9660.
10. For example: Zuo, G.; Louie, J. Angew. Chem., Int. Ed. 2004, 43, 2277-2279.
11. (a) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871-2874.
12. (b) Burgess, K. Tetrahedron Lett. 1985, 26, 3049-3052.
13. (c) Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1985, 26, 3825-3828.
14. (d) Yamamoto, K.; Ishida, T.; Tsuji, J. Chem. Lett. 1987, 1157-1158.
15. (e) Hirio, K.; Arinaga, Y.; Ogino, T. Chem. Lett. 1992, 2329-2332.
16. Vardapetyan, A. A.; Khachatryan, D. S.; Panosyan, G. A.; Morlyan, N. M. J. Org. Chem. USSR 1986, 22, 2034-2037.
17. Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Tolstikov, G. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990, 39, 1447-1450.
18. (a) Pohlhaus, P. D.; Bowman, R. K.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 2294-2295.
19. (b) Pohlhaus, P. D.; Johnson, J. S. J. Org. Chem. 2005, 70, 1057-1059.
20. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023-3026.
21. McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094-12095.
22. 3 (19%, 18 h), quinuclidine (14%, 18 h).
23. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
24. Hayashi, T.; Yamane, M.; Ohno, A. J. Org. Chem. 1997, 62, 204-207.