Generation of α,β-unsaturated platinum carbenes from homopropargylic alcohols: Rearrangements to polysubstituted furans

Organic Letters

Volumn 13, Issue 21, 2011, Pages 5924-5927

  Allegretti, Paul A ^a   Ferreira, Eric M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80055096926     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202649j     Document Type: Article

References (49)

1. Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271-2296
2. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449
3. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211
4. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265
5. Arcadi, A. Chem. Rev. 2008, 108, 3266-3325
6. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326-3350
7. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378
8. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395-3442
9. Shen, H. C. Tetrahedron 2008, 64, 3885-3903
10. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208-3221
11. Rooke, D. A.; Ferreira, E. M. J. Am. Chem. Soc. 2010, 132, 11926-11928
12. Kirsch, S. F. Synthesis 2008, 3183-3204
13. See ref 1h.
14. Dudnik, A. S.; Xia, Y.; Li, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 7645-7655
15. Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440-1452
16. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966-5968
17. Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089-13102
18. Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687-7692
19. Hashmi, A. S. K.; Schwarz, L.; Choi, J. -H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288
20. Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409-5412
21. Yoshida, M.; Al-Amin, M.; Shishido, K. Synthesis 2009, 2454-2466
22. Barluenga, J.; Riesgo, L.; Vicente, R.; López, L. A.; Tomás, M. J. Am. Chem. Soc. 2008, 130, 13528-13529
23. Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3925-3927
24. Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4531-4534
25. Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164-11165
26. Marshall, J. A.; Robinson, E. D. J. Org. Chem. 1990, 55, 3450-3451
27. Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655-3661
28. Aponick, A.; Li, C. -Y.; Malinge, J.; Marques, E. F. Org. Lett. 2009, 11, 4624-4627
29. Egi, M.; Azechi, K.; Akai, S. Org. Lett. 2009, 11, 5002-5005 and the references therein
30. Schmuck, C.; Rupprecht, D. Synthesis 2007, 3095-3110
31. Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076-2080
32. Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850-852
33. Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238-6241
34. Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955-2020
35. A recent report described a similar mode of carbene generation toward the formation of polycyclic compounds via [3 + 2] cycloadditions. See: Saito, K.; Sogou, H.; Suga, T.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 689-691
36. Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260-11261
37. Hiroya, K.; Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349-5352
38. Xia, Y.; Huang, G. J. Org. Chem. 2010, 75, 7842-7854
39. Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354-7358
40. Nakamura, I.; Bajracharya, G. B.; Wu, H.; Oishi, K.; Mizushima, Y.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 15423-15430
41. Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022-15023
42. Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752
43. Gold catalysts also displayed reactivity, but the hydroalkoxylation product (ii) was the major component. This observation is consistent with the lesser metal-based donation that is generally seen in catalytic Au systems relative to Pt. For a relevant discussion, see: Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395-403
44. We considered the possibility that compound ii was an intermediate toward the furan product under the Pt-catalyzed conditions. Although enol ether ii could be observed as a product at low temperature, subjecting it to the reaction conditions, as well as multiple variants of these conditions, never produced furan 8. See the Supporting Information for details.
45. Creary, X.; Butchko, M. A. J. Org. Chem. 2002, 67, 112-118
46. Creary, X.; Butchko, M. A. J. Org. Chem. 2001, 66, 1115-1121
47. Creary, X.; Wang, Y. -X. Tetrahedron Lett. 1989, 30, 2493-2496
48. For a review on the synthetic utility of silylfurans, see: Keay, B. A. Chem. Soc. Rev. 1999, 28, 209-215
49. This hypothesis is consistent with DFT calculation studies evaluating the migratory processes of hydrogen and bromine in the gold-catalyzed synthesis of furans. See: Xia, Y.; Dudnik, A. S.; Gevorgyan, V.; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940-6941