Gold(I)-catalyzed oxidative rearrangements

Journal of the American Chemical Society

Volumn 129, Issue 18, 2007, Pages 5838-5839

  Witham, Cole A ^a   Mauleón, Pablo ^a   Shapiro, Nathan D ^a   Sherry, Benjamin D ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; CYCLOPROPANE DERIVATIVE; GOLD; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY;

CATALYSIS; GOLD; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 34248597739     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071231+     Document Type: Article

References (35)

1. (a) Nieto-Oberhuber, C,; Mun̄oz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
2. (b) Mamane, V.; Gress, T.; Krause, H.; Furstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
3. (c) Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546.
4. (d) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
5. (e) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
6. (f) Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442.
7. (g) Horino, Y.; Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 11364.
8. (h) Lee, J. H.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 912.
9. For a review see: (i) Gorin, D. J.; Toste, F. D. Nature, 2007, 446, 395.
10. (a) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505.
11. (b) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc 2005, 127, 18002.
12. (c) Gorin, D. J.; Dube, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 14480.
13. (d) López, S.; Herrero-Gómez, E.; Pérez- Galán, P.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 6029.
14. For oxidation of ruthenium-carbenoid intermediates with N-hydroxyimides in ruthenium-catalyzed cycloisomerizations see: (a) Trost, B. M.; Rhee, Y.-H. J. Am. Chem. Soc. 1999, 121, 11680.
15. (b) Trost, B. M.; Rhee, Y.-H. J. Am. Chem. Soc. 2002, 124, 2528.
16. Oda, R.; Mieno, M.; Hayashi, Y. Tetrahedron Lett. 1967, 2363.
17. (a) Dost, F.; Gosselck, J. Tetrahedron Lett. 1970, 5091.
18. (b) Takebayashi, M.; Kashiwada, T.; Hamaguchi, M.; Ibata, T. Chem. Lett. 1973, 809.
19. (c) Moody, C. J.; Slawin, A. M. Z.; Taylor, R. J.; Williams, D. J. Tetrahedron Lett. 1988, 29, 6009.
20. 2, 60%; oxone, 86%).
21. De Fremont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 2411.
22. Cyclopropylaldehyde 5c was observed as a by-product (3-10%) in the cycloisomerization of 1c catalyzed by palladium or platinum. Nevado, C.; Charrualt, L.; Michelet, V.; Nieto-Oberhuber, C.; Muñoz, M. P.; Méndez, M.; Rager, M.-N.; Genêt, J.-P.; Echavarren, A. M. Eur J. Org. Chem. 2003, 706.
23. An alternative mechanism involves trapping of the intermediate by water, to give alcohol 28, and subsequent oxidation to the aldehyde; however, alcohol 28 was not oxidized under the reaction conditions. (Chemical Equation Presented)
24. For gold-catalyzed reaction of ct-diazoesters see: (a) Fructos, M. R.; Belderrain, T. R.; de Frémont, P.; Scott, N. M.; Díaz-Requejo, N. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284.
25. (b) Fructos, M. R.; de Frémont, P.; Díaz-Requejo, N. M.; Pérez, P. J. Organometallics 2006, 25, 2237.
26. Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
27. 3) leads to the formation of dione 29; however, 29 was not oxidized to 20b under the reaction conditions. (Chemical Equation Presented)
28. 15 however, the ketoaldehyde corresponding to trapping of α-ketocarbenoid intermediate (see eq. 4) was not observed.
29. 2, 35%.
30. 2) rearrangement of 18b afforded 20b in 41% yield.
31. Lataoka, H.; Watanabe, K.; Goto, K. Tetrahedron Lett. 1990, 31, 4181.
32. 3 did not induce isomerization to (E)-27.
33. For examples of reactions showing different reactivity when gold(I) and gold(III) complexes are employed as catalysts see: (a) Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500.
34. (b) Lemiére, G.; Gandom, V.; Agenet, N.; Goddard, J.-P.; de Kozak, A.; Aubert, C.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2006, 45, 7596.
35. (c) Hashmi, A. S. K.; Salathe, R.; Frey, W. Chem.-Eur. J. 2006, 12, 6991.