Catalytic migratory oxidative coupling of nitrones

Organic Letters

Volumn 13, Issue 16, 2011, Pages 4288-4291

  Hashizume, Shogo ^a   Oisaki, Kounosuke ^a   Kanai, Motomu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; CUPROUS IODIDE; IODIDE; NITROGEN OXIDE; NITRONES;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

CATALYSIS; COPPER; IODIDES; MOLECULAR STRUCTURE; NITROGEN OXIDES; OXIDATION-REDUCTION;

EID: 80051703423     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201629n     Document Type: Article

References (55)

1. Topics in Current Chemistry; Yu, J.-Q., Shi, Z.-J., Eds.; Springer: New York, 2010; Vol. 292.
2. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439
3. Davies, H. M. L.; Du Bois, J.; Yu, J. -Q. Chem. Soc. Rev. 2011, 40, 1855
4. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
5. Scheuermann, C. J. Chem. Asian. J. 2010, 5, 436
6. Klussmann, M.; Sureshkumar, D. Synthesis 2011, 353
7. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
8. Baran, P. S.; Maimone, T. J.; Richter, J. M. Nature 2007, 446, 404
9. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854
10. Ishihara, Y.; Baran, P. S. Synlett 2010, 1733
11. Godula, K.; Sames, D. Science 2006, 312, 67
12. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
13. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
14. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
15. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 10.1039/c1cs15083a
16. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672
17. Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 3173
18. Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. 2006, 45, 1949
19. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56
20. Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075
21. Li, Z.-P.; Yu, R.; Li, H.-J. Angew. Chem., Int. Ed. 2008, 47, 7497
22. Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901
23. Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090
24. Dubs, C.; Hamashima, Y.; Sasamoto, N.; Seidel, T. M.; Suzuki, S.; Hashizume, D.; Sodeoka, M. J. Org. Chem. 2008, 73, 5859
25. Richter, H; Mancheño, O. G. Eur. J. Org. Chem. 2010, 4460
26. Yang, F.; Li, J.; Xie, J.; Huang, Z.-Z. Org. Lett. 2010, 12, 5214
27. Xie, J.; Huang, Z.-Z. Angew. Chem., Int. Ed. 2010, 49, 10181
28. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810
29. Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997
30. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968
31. Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8928. Also see refs 2, 5a, 5b, 5d, 5e, 5k, and 5l
32. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137
33. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863
34. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887
35. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023
36. Stevens, A. C.; Palmer, C.; Pagenkopf, B. L. Org. Lett. 2011, 13, 1528
37. Kinugasa, M.; Hashimoto, S. J. Chem. Soc., Chem. Commun. 1972, 466
38. Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999
39. Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572
40. Marco-Contelles, J. Angew. Chem., Int. Ed. 2004, 43, 2198
41. Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245
42. Pinet, S.; Pandya, S. U.; Chavant, P. Y.; Ayling, A.; Vallee, Y. Org. Lett. 2002, 4, 1463
43. Garret, M. R.; Tarr, J. C.; Johnson, J. S. J. Am. Chem. Soc. 2007, 129, 12944
44. Murarka, S.; Studer, A. Org. Lett. 2011, 13, 2746
45. Yet, L. Tetrahedron 1999, 55, 9349
46. Yet, L. Chem. Rev. 2000, 100, 2963
47. Intriguing properties of oxetanes in medicinal chemistry: Burk-hard, J. A.; Wuitschik, G.; Rogers-Evans, M.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 9052
48. Kabalka, G. W.; Brown, H. C.; Suzuki, A.; Honma, S.; Arase, A.; Itoh, M. J. Am. Chem. Soc. 1970, 92, 710
49. Miyabe, H.; Ueda, M.; Naito, T. J. Org. Chem. 2000, 65, 5043
50. Liu, J.-Y.; Jang, Y.-J.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Org. Chem. 2003, 68, 4030
51. Akindele, T.; Yamada, K.-i.; Tomioka, K. Acc. Chem. Res. 2009, 42, 345. Also see Supporting Information for our detailed investigations
52. Lal, D.; Griller, D.; Husband, S.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 6355
53. Mailard, B.; Forrest, D.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7024
54. Detailed mechanism of Fenton reaction is still under debate. For recent discussion: Rachmilovic-Calis, S.; Masarwa, A.; Meyerstein, N.; Meyerstein, D.; van Ekdik, R. Chem.-Eur. J. 2009, 15, 8303 and references therein
55. Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106