Gold(I)-catalyzed intramolecular rearrangement of vinylidenecyclopropanes

Journal of Organic Chemistry

Volumn 73, Issue 21, 2008, Pages 8344-8347

  Shi, Min ^a   Wu, Lei ^a   Lu, Jian Mei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; CONTROL EXPERIMENTS; FUNCTIONALIZED; GOLD CATALYSTS; INTRAMOLECULAR REARRANGEMENTS; MILD CONDITIONS; REARRANGEMENT MECHANISMS;

GOLD COMPOUNDS;

CYCLOPROPANE DERIVATIVE; GOLD COMPLEX; NAPHTHALENE DERIVATIVE; VINYL DERIVATIVE; VINYLIDENE CHLORIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; THERMODYNAMICS;

EID: 55249121856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801579b     Document Type: Article

References (30)

1. For a recent review on the chemistry of vinylidenecyclopropanes, see: (a) Maeda, H.; Mizuno, K. J. Synth. Org. Chem. Jpn. 2004, 62, 1014-1025.
2. (b) Isagawa, K.; Mizuno, K.; Sugita, H.; Otsuji, Y. J. Chem. Soc., Perkin Trans. 1 1991, 2283-2285, and references therein.
3. (c) Al-Dulayymi, J. R.; Baird, M. S. J. Chem. Soc., Perkin Trans. 1 1994, 1547-1548.
4. (a) Maeda, H.; Hirai, T.; Sugimoto, A.; Mizuno, K. J. Org. Chem. 2003, 68, 7700-7706.
5. (b) Pasto, D. J.; Brophy, J. E. J. Org. Chem. 1991, 56, 4554-4556.
6. (c) Sugita, H.; Mizuno, K.; Saito, T.; Isagawa, K.; Otsuji, Y. Tetrahedron Lett. 1992, 33, 2539-2542.
7. (d) Mizuno, K.; Sugita, H.; Kamada, T.; Otsuji, Y. Chem. Lett. 1994, 449-452, and references therein.
8. (e) Stepakov, A. V.; Larina, A. G.; Molchanov, A. P.; Stepakova, L. V.; Starova, G. L.; Kostikov, R. R. Russ. J. Org. Chem. 2007, 43, 41-49.
9. (f) Poutsma, M. L.; Ibarbia, P. A. J. Am. Chem. Soc. 1971, 93, 440-450.
10. (g) Hendrick, M. E.; Hardie, J. A.; Jones, M. J. Org. Chem. 1971, 36, 3061-3062.
11. (a) Xu, G.-C.; Liu, L.-P.; Lu, J.-M.; Shi, M. J. Am. Chem. Soc. 2005, 127, 14552-14553.
12. (b) Xu, G.-C.; Ma, M.; Liu, L.-P.; Shi, M. Synlett 2005, 1869-1872.
13. (c) Zhang, Y.-P.; Lu, J.-M.; Xu, G.-C.; Shi, M. J. Org. Chem. 2007, 72, 509-516.
14. (d) Lu, J.-M.; Shi, M. Org. Lett. 2007, 9, 1805-1808.
15. (e) Lu, J.-M.; Shi, M. Org. Lett. 2006, 8, 5317-5320.
16. (f) Lu, J.-M.; Shi, M. Tetrahedron 2007, 63, 7545-7549.
17. (g) Fitjer, L. Angew. Chem., Int. Ed. Engl. 1975, 14, 360-361.
18. (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3183.
19. (b) Jimémez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
20. (c) Fürster, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
21. (d) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
22. (e) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750.
23. (f) Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200.
24. (g) Hoffmann-Röder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387.
25. (h) Arcadi, A.; Di Giuseppe, S. Curr. Org. Chem. 2004, 8, 795.
26. (i) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431.
27. (a) Fleming, I. Chemtracts: Org. Chem. 2001, 14, 405-406.
28. (b) Kozikowski, A. P.; Ames, A. J. Am. Chem. Soc. 1980, 102, 860.
29. (c) Hoffmann, H. M. R.; Tsushima, T. J. Am. Chem. Soc. 1977, 99, 6008.
30. (d) Snider, B.; Jackson, A. J. Org. Chem. 1982, 47, 5393.