TBHP/I2-mediated domino oxidative cyclization for one-pot synthesis of polysubstituted oxazoles

Organic Letters

Volumn 12, Issue 23, 2010, Pages 5561-5563

  Jiang, Huanfeng ^a   Huang, Huawen ^a   Cao, Hua ^a   Qi, Chaorong ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650323348     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1023085     Document Type: Article

References (43)

1. Ignatius, J. T.; Michael, J. S. Chem. Rev. 1975, 75, 389
2. Jin, Z. Nat. Prod. Rep. 2009, 26, 382
3. Vedejs, E.; Barda, D. A. Org. Lett. 2000, 2, 1033
4. Atkins, J. M.; Vedejs, E. Org. Lett. 2005, 7, 3351
5. Zhang, J. M.; Ciufolini, M. A. Org. Lett. 2009, 11, 2389
6. Wipf, P. Chem. Rev. 1995, 95, 2115
7. Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126
8. Shin-ya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262
9. Dalisay, D. S.; Rogers, E. W.; Edison, A. S.; Molinski, T. F. J. Nat. Prod. 2009, 72, 732
10. Hagelueken, G.; Albrecht, S. C.; Steinmetz, H.; Jansen, R.; Heinz, D. W.; Kalesse, M.; Schubert, W. D. Angew. Chem., Int. Ed. 2009, 48, 595
11. Riego, E.; Hernandez, D.; Albericio, F.; Alvarez, M. Synthesis 2005, 12, 1907
12. Jin, Z. Nat. Prod. Rep. 2006, 23, 464
13. Rosener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846
14. Lee, J. C.; Kim, S.; Lee, Y. C. Synth. Commun. 2003, 33, 1611
15. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604
16. Yeh, V. Tetrahedron 2004, 60, 11995
17. Nesi, R.; Turchi, S.; Giomi, D. J. Org. Chem. 1996, 61, 7933
18. Mendelsohn, B. A.; Lee, S.; Kim, S.; Teyssier, F.; Aulakh, V. S.; Ciufolini, M. A. Org. Lett. 2009, 11, 1539
19. Meyers, A. I.; Tavares, F. Tetrahedron Lett. 1994, 35, 2481
20. Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165
21. Meyers, A. I.; Tavares, F. X. J. Org. Chem. 1996, 61, 8207
22. Besselieivre, F.; Piguel, S. Angew. Chem., Int. Ed. 2009, 48, 9553
23. Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2006, 8, 2495
24. Lee, K.; Counceller, C. M.; Stambuli, J. P. Org. Lett. 2009, 11, 1457
25. Williams, D. R.; Fu, L. F. Org. Lett. 2010, 12, 808
26. Wan, C. F.; Zhang, J. T.; Wang, S. J.; Fan, J. M.; Wang, Z. Y. Org. Lett. 2010, 12, 2338
27. Pan, Y. M.; Zheng, F. J.; Lin, H. X.; Zhan, Z. P. J. Org. Chem. 2009, 74, 3148
28. Wan, C. F.; Gao, L. F.; Wang, Q.; Zhang, J. T.; Wang, Z. Y. Org. Lett. 2010, 12, 3902
29. Verrier, C.; Martin, T.; Hoarau, C.; Marsais, F. J. Org. Chem. 2008, 73, 7383
30. Besselieivre, F.; Piguel, S.; Betzer, F. M.; Grierson, D. S. Org. Lett. 2008, 10, 4029
31. Tietze, L. F. Chem. Rev. 1996, 96, 115
32. Ikeda, S. Acc. Chem. Res. 2000, 33, 511
33. Enders, D. C.; Wang, J. W. Angew. Chem. 2008, 120, 7649
34. Cao, H.; Jiang, H. F.; Yao, W. J.; Liu, X. H. Org. Lett. 2009, 11, 1931
35. Liu, W. B.; Jiang, H. F.; Zhang, M.; Qi, C. R. J. Org. Chem. 2010, 75, 966
36. Cao, H.; Jiang, H. F.; Mai, R. H.; Zhu, S. F.; Qi, C. R. Adv. Synth. Catal. 2010, 352, 143
37. Wang, A. Z.; Jiang, H. F. J. Org. Chem. 2010, 75, 2321
38. Around half of benzylamine was oxidized to benzaldehyde detected by GC-MS.
39. Aliphatic alkenes, such as 1-octene and methyl acrylate, could not give the corresponding products as well.
40. When the mixture of styrene 1a (1 equiv), TBHP (1 equiv), and iodine (1 equiv) in dichloromethane was stirred at room temperature for 4 h, compound A was obtained in 92% yield.
41. Kornblum, N.; Powers, J. W.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562
42. Yin, G. D.; Zhou, B. H.; Meng, X. G.; Wu, A. X.; Pan, Y. J. Org. Lett. 2006, 8, 2245
43. Reaction of B and 2a under the reaction conditions as 1a and 2a afforded the desired product (3aa) in high yield (94%).