Unexpected C-C bond cleavage: Synthesis of 1,2,4-oxadiazol-5-ones from amidoximes with pentafluorophenyl or trifluoromethyl anion acting as leaving group

Organic Letters

Volumn 13, Issue 23, 2011, Pages 6172-6175

  Gerfaud, Thibaud ^a   Wei, Hai Long ^a   Neuville, Luc ^a   Zhu, Jieping ^a,b  

^a CNRS   (France)

^b EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 82355187594     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202554m     Document Type: Article

References (54)

1. Sattler, A.; Parkin, G. Nature 2010, 463, 523-526
2. For a review, see: Prantz, K.; Mulzer, J. Chem. Rev. 2010, 110, 3741-3766
3. Quesnel, Y.; Toupet, L.; Duhamel, L.; Duhamel, P.; Poirier, J. M. Tetrahedron: Asymmetry 1999, 10, 1015-1018
4. Kwart, H.; King, K. Chem. Rev. 1968, 68, 415-447
5. Stajer, G.; Csende, F.; Fueloep, F. Curr. Org. Chem. 2003, 7, 1423-1432
6. Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2009, 82, 778-792
7. Lutz, R. P. Chem. Rev. 1984, 84, 205-247
8. Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2011, 50, 7740-7752
9. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100-1105
10. Bonesi, S. M.; Fagnoni, M. Chem.-Eur. J. 2010, 16, 13572-13589
11. Necas, D.; Kotora, M. Curr. Org. Chem. 2007, 11, 1566-1591
12. Jun, C.-H.; Park, J.-W. Top. Organomet. Chem. 2007, 24, 117-143
13. Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1-20
14. Takahashi, T.; Kuzuba, Y.; Kong, F.; Nakajima, K.; Xi, Z. J. Am. Chem. Soc. 2005, 127, 17188-17189
15. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870-883
16. Ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Rev. 2004, 104, 4105-4123
17. Fuson, R. C.; Bull, B. A. Chem. Rev. 1934, 15, 275-309
18. Nicolaou, K. C.; Adsol, V. A.; Hale, C. R. H. Org. Lett. 2010, 12, 1552-1555 and reference cited herein
19. Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321-2326
20. Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. J. Am. Chem. Soc. 2009, 131, 1382-1383 and references cited therein
21. For a review, see: Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399-1422
22. For a recent example of an LDA catalyzed Haller-Bauer reaction, see: Ishihara, K.; Yano, T. Org. Lett. 2004, 6, 1983-1986
23. Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030-5048
24. Nakai, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2011, 133, 11066-11068
25. Chiba, S.; Zhang, L.; Ang, G. Y.; Hui, B. W.-Q. Org. Lett. 2010, 12, 2052-2055
26. Gerfaud, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 572-577
27. Zaman, S.; Mitsuru, K.; Abell, A. D. Org. Lett. 2005, 7, 609-611
28. Kitamura, M.; Narasaka, K. Chem. Record 2002, 2, 268-277
29. Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 4505-4519
30. Substituted cyclopentadienyl anion as a leaving group; see: Fisher, E. L; Lambert, T. H. Org. Lett. 2009, 11, 4108-4110
31. Acetylide as a leaving group; see: Sugiishi, T.; Kimura, A.; Nakamura, H. J. Am. Chem. Soc. 2010, 132, 5332-5333
32. 1,3-Dicarbonyl group as a leaving group; see: Li, H.; Li, W.; Liu, W.; He, Z.; Li, Z. Angew. Chem., Int. Ed. 2011, 50, 2975-2978
33. 3 in MeOH, see: Neufeldt, S. R.; Sanford, M. S. Org. Lett. 2010, 12, 532-535
34. Garner, C. M.; Fisher, H. C. Tetrahedron Lett. 2006, 47, 7405-7407
35. Fisher, H. C., PhD Thesis, Baylor University, 2006.
36. Bolton, R. E.; Coote, S. J.; Finch, H.; Lowdon, A.; Pegg, N.; Vinader, M. V. Tetrahedron Lett. 1995, 36, 4471-4474
37. Wustrow, D. J.; Belliotti, T. R.; Capiris, T.; Kneen, C. O.; Bryans, J. S.; Field, M. J.; Williams, D.; El-Kattan, A.; Buchholz, L.; Kinsora, J. J.; Lotarski, S. M.; Vartanian, M. G.; Taylor, C. P.; Donevan, S. D.; Thorpe, A. J.; Schwarz, J. B. Bioorg. Med. Chem. Lett. 2009, 19, 247-250
38. Dianna, G. D.; Volkots, D. L.; Nitz, T. J.; Bailey, T. R.; Long, M. A.; Vescio, N.; Aldous, S.; Pevear, D. C.; Dutko, F. J. J. Med. Chem. 1994, 37, 2421-2436
39. von Wantoch Rekowski, M.; Pyriochou, A.; Papapetropoulos, N.; Stössel, A.; Papapetropoulos, A.; Giannis, A. Bioorg. Med. Chem. 2010, 18, 1288-1296
40. Brown, H. C.; Wetzel, C. R. J. Org. Chem. 1965, 30, 3734-3738
41. Wang, Y.; Miller, R. L.; Sauer, D. R.; Djuric, S. W. Org. Lett. 2005, 7, 925-928
42. Buscemi, S.; Pace, A.; Piccionello, A. P.; Pibiri, I.; Vivona, N. Heterocycles 2004, 63, 1619-1628
43. Marques, C. A.; Selva, M.; Tundo, P.; Montanari, F. J. Org. Chem. 1993, 58, 5765-5770
44. Pereira, M. M. A.; Pedro Paulo, S. In The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids; Rappoport, Z.,; Liebman, J. F., Eds.; Wiley: 2008; pp 343-498.
45. Lemmens, J. M.; Blommerde, W. J. M.; Thijs, L.; Zwaneburg, B. J. Org. Chem. 1984, 49, 2231-2235
46. Mandal, A. B.; Gomez, A.; Trujillo, G.; Méndez, F.; Jiménez, H. A.; de Jesus Morales, M.; Martinez, R.; Delgado, F.; Tamariz, J. J. Org. Chem. 1997, 62, 4105-4115
47. Prager, J. H.; Ogden, P. H. J. Org. Chem. 1968, 33, 2100-2102
48. Han, C.; Kim, E. H.; Colby, D. A. J. Am. Chem. Soc. 2011, 133, 5802
49. Riofdki, M. V.; John, J. P.; Zheng, M. M.; Kirshner, J.; Colby, D. A. J. Org. Chem. 2011, 76, 3676-3683
50. Fioravanti, S.; Pellacani, L.; Ramadori, F.; Tardella, P. A. Tetrahedron Lett. 2007, 48, 7821-7824
51. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959-1964
52. See ref 26.
53. Olivella, S.; Sole, A.; Jimenez, O.; Bosch, M. P.; Guerrero, A. J. Am. Chem. Soc. 2005, 127, 2620-2627
54. Cordaro, J. G.; Bergman, G. J. Am. Chem. Soc. 2004, 126, 16912-16929