Copper-catalyzed synthesis of trisubstituted isoxazoles via a cascade cyclization-migration process

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9344-9351

  Ueda, Masafumi ^a   Sugita, Shoichi ^a   Sato, Aoi ^a   Miyoshi, Tetsuya ^a   Miyata, Okiko ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; INTRAMOLECULAR ADDITIONS; ISOXAZOLES; OXIME ETHERS; REGIOSELECTIVE SYNTHESIS;

ACETYLENE; ETHERS;

CYCLIZATION;

ALKYNYL GROUP; CHLOROBENZENE; COPPER; ETHER DERIVATIVE; ISOXAZOLE DERIVATIVE; METHYL GROUP; OXIME; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CYCLIZATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; ISOXAZOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84867714798     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301358h     Document Type: Article

References (50)

1. Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K.; Joule, J. Comprehensive Heterocyclic Chemistry III; Elsevier: Oxford, 2008.
2. Carlsen, L.; Döpp, D.; Döpp, H.; Duus, F.; Hartmann, H.; Lang-Fugmann, S.; Schulze, B.; Smalley, R. K.; Wakefield, B. J. In Houben-Weyl Methods in Organic Chemistry; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1992; Vol. E8a, p 45.
3. Sperry, J.; Wright, D. Curr. Opin. Drug Discov. Devel. 2005, 8, 723
4. Burrows, A. D.; Frost, C. G.; Mahon, M. F.; Raithby, P. R.; Richardson, C.; Stevenson, A. J. Chem. Commun. 2010, 46, 5064
5. Lee, Y.; Koyama, Y.; Yonekawa, M.; Tanaka, T. Macromolecules 2009, 42, 7709
6. Wakefield, B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Shaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 11, p 229.
7. Jäger, V.; Colinas, P. A. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Ed.; Wiley: Hoboken, 2002; Vol. 59, p 361.
8. Sanders, B. C.; Friscourt, F.; Ledin, P. A.; Mbua, N. E.; Arumugam, S.; Guo, J.; Boltje, T. J.; Popik, V. V.; Boons, G.-J. J. Am. Chem. Soc. 2011, 133, 949
9. Budzik, B. W.; Evans, K. A.; Wisnoski, D. D.; Jin, J.; Rivero, R. A.; Szewczyk, G. R.; Jayawickreme, C.; Moncol, D. L.; Yu, H. Bioorg. Med. Lett. 2010, 20, 1363
10. Wang, L.; Yu, X.; Feng, X.; Bao, M. Org. Lett. 2012, 14, 2418
11. Dadiboyena, S.; Nefzi, A. Tetrahedron Lett. 2012, 53, 2096
12. Dissanayake, A. A.; Odom, A. L. Tetrahedron 2012, 68, 807
13. Burhard, J. A.; Tchitchanov, B. H.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 5379
14. Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643
15. Okitsu, T.; Potewar, T. M.; Wada, A. J. Org. Chem. 2011, 76, 3438
16. Denmark, S. E.; Kallemeyn, J. M. J. Org. Chem. 2005, 70, 2839
17. Kumar, J. S. D.; Ho, M. M.; Leung, J. M.; Toyokuni, T. Adv. Synth. Catal. 2002, 344, 1146
18. Moore, J. E.; Davies, M. W.; Goodenough, K. M.; Wybrow, R. A. J.; York, M.; Johnson, C. N.; Harrity, J. P. A. Tetrahedron 2005, 61, 6707
19. Jackowski, O.; Lecourt, T.; Micouin, L. Org. Lett. 2011, 13, 5664
20. She, Z.; Niu, D.; Chen, L.; Gunawan, M. A.; Shanja, X.; Hersh, W. H.; Chen, Y. J. Org. Chem. 2012, 77, 3627
21. Gayon, E.; Quinonero, O.; Lemouzy, S.; Vrancken, E.; Campagne, J.-M. Org. Lett. 2011, 13, 6418
22. Nishiwaki, N.; Kobiro, K.; Hirao, S.; Sawayama, J.; Saigo, K.; Ise, Y.; Nishizawa, M.; Ariga, M. Org. Biomol. Chem. 2012, 10, 1987
23. Kawai, H.; Sugita, Y.; Tokunaga, E.; Shibata, N. Eur. J. Org. Chem. 2012, 1295
24. Xiang, D.; Xin, X.; Liu, X.; Zhang, R.; Yang, J.; Dong, D. Org. Lett. 2012, 14, 644
25. Hashimoto, Y.; Takada, A.; Takikawa, H.; Suzuki, K. Org. Biomol. Chem. 2012, 10, 6003
26. Lipshutz, B. H.; Yamamoto, Y., Eds. Chem. Rev. 2008, 108, 3239.
27. Kirsch, S. F. Synthesis 2008, 3183
28. Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994
29. Corma, C.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
30. Manarin, F.; Roehr, J. A.; Gay, R. M.; Brandao, R.; Menezes, P. H.; Nogueira, C. W.; Zeni, G. J. Org. Chem. 2009, 74, 2153
31. Fürstner, A.; Heilmann, E. K.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 4760
32. Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022
33. Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024
34. Takaya, J.; Udagawa, S.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4906
35. Li, G.; Huang, X.; Zhang, L. Angew. Chem., Int. Ed. 2008, 47, 346
36. Nakamura, I.; Yamagishi, U.; Song, D.; Konta, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 2284
37. Cariou, K.; Ronan, B.; Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2007, 46, 1881
38. Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546
39. Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 2649
40. Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473
41. Cheong, J. Y.; Im, D.; Lee, M.; Lim, W.; Rhee, Y. H. J. Org. Chem. 2011, 76, 324
42. Nakamura, I.; Chan, C. S.; Araki, T.; Terada, M.; Yamamoto, Y. Adv. Synth. Catal. 2009, 351, 1089
43. Peng, L.; Zhang, X.; Ma, M.; Wang, J. Angew. Chem., Int. Ed. 2007, 46, 1905
44. Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863
45. Wang, Y.-M.; Kuzniewski, C. N.; Rauniyar, V.; Hoong, C.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 12972
46. Komeyama, K.; Takahashi, K.; Takai, K. Org. Lett. 2008, 10, 5119
47. Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 3181
48. For the related gold-catalyzed synthesis of isoxazoles, see: Nakamura, I.; Okamoto, M.; Terada, M. Org. Lett. 2010, 12, 2453
49. Ueda, M.; Ikeda, Y.; Sato, A.; Ito, Y.; Kakiuchi, M.; Shono, H.; Miyoshi, T.; Naito, T.; Miyata, O. Tetrahedron 2011, 67, 4612
50. Those conditions were previously used in a domino reaction involving a cyclization and Claisen-type [3,3]-sigmatropic rearrangement; see: Ueda, M.; Sato, A.; Ikeda, Y.; Miyoshi, T.; Naito, T.; Miyata, O. Org. Lett. 2010, 12, 2594