Divergent reaction pathways of a cationic intermediate: Rearrangement and cyclization of 2-substituted furyl and benzofuryl enones catalyzed by iridium(III)

Journal of the American Chemical Society

Volumn 133, Issue 10, 2011, Pages 3300-3303

  Vaidya, Tulaza ^a   Manbeck, Gerald F ^a   Chen, Sylvia ^a   Frontier, Alison J ^a   Eisenberg, Richard ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; CATIONIC INTERMEDIATES; CYCLOHEXANONES; ELECTROCYCLIZATION; ELECTROPHILICITY; FRIEDEL-CRAFTS ALKYLATION; MALONATES; QUATERNARY CENTERS; REACTION PATHWAYS;

IRIDIUM; IRIDIUM COMPOUNDS; REACTION INTERMEDIATES;

CYCLIZATION;

CYCLOHEXANONE DERIVATIVE; IRIDIUM; PYRROLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; FRIEDEL CRAFTS REACTION;

EID: 79952595343     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja111317q     Document Type: Article

References (47)

1. For reviews of the Nazarov reaction, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642
2. Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1
3. Harmata, M. Chemtracts 2004, 17, 416
4. Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577
5. Tius, M. A. Eur. J. Org. Chem. 2005, 2193
6. Pellissier, H. Tetrahedron 2005, 61, 6479
7. For accounts of the polarized Nazarov reaction, see: He, W.; Herrick, I. R.; Atesin, T. A.; Caruana, P. A.; Kellenberger, C. A.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 1003
8. He, W.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2003, 125, 14278
9. For examples of catalysis with polarized enones, see: Janka, M.; He, W.; Frontier, A. J.; Eisenberg, R. J. Am. Chem. Soc. 2004, 126, 6864
10. Janka, M.; He, W.; Frontier, A. J.; Flaschenriem, C.; Eisenberg, R. Tetrahedron 2005, 61, 6193
11. Janka, M.; He, W.; Haedicke, I. E.; Fronczek, F. R.; Frontier, A. J.; Eisenberg, R. J. Am. Chem. Soc. 2006, 128, 5312
12. Malona, J. A.; Colbourne, J. M.; Frontier, A. J. Org. Lett. 2006, 8, 5661
13. Nie, J.; Zhu, H.-W.; Cui, H.-F.; Hua, M.-Q.; Ma, J.-A. Org. Lett. 2007, 9, 3053
14. Huang, J.; Frontier, A. J. J. Am. Chem. Soc. 2007, 129, 8060
15. Walz, I.; Bertogg, A.; Togni, A. Eur. J. Org. Chem. 2007, 2650
16. Walz, I.; Togni, A. Chem. Commun. 2008, 4315
17. Marcus, A. P.; Lee, A. S.; Davis, R. L.; Tantillo, D. J.; Sarpong, R. Angew. Chem., Int. Ed. 2008, 47, 6379
18. Kawatsura, M.; Higuchi, Y.; Hayase, S.; Nanjo, M.; Itoh, T. Synlett 2008, 1009
19. He, W.; Huang, J.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2007, 129, 498
20. He, W.; Huang, J.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 300
21. Fujiwara, M.; Kawatsura, M.; Hayase, S.; Nanjo, M.; Itoh, T. Adv. Synth. Catal. 2009, 351, 123
22. Bachu, P.; Akiyama, T. Bioorg. Med. Chem. Lett. 2009, 19, 3764
23. Malona, J. A.; Cariou, K.; Frontier, A. J. J. Am. Chem. Soc. 2009, 131, 7560
24. Bitar, A. Y.; Frontier, A. J. Org. Lett. 2009, 11, 49
25. Vaidya, T.; Atesin, A. C.; Herrick, I. R.; Frontier, A. J.; Eisenberg, R. Angew. Chem., Int. Ed. 2010, 49, 3363
26. Cao, P.; Deng, C.; Zhou, Y.-Y.; Sun, X.-L.; Zheng, J.-C.; Xie, Z.; Tang, Y. Angew. Chem., Int. Ed. 2010, 49, 4463
27. Atesin, A. C.; Zhang, J.; Vaidya, T.; Brennessel, W. W.; Frontier, A. J.; Eisenberg, R. Inorg. Chem. 2010, 49, 4331
28. Zhang, J.; Vaidya, T.; Brennessel, W. W.; Frontier, A. J.; Eisenberg, R. Organometallics 2010, 29, 3341
29. Murugan, K.; Srimurugan, S.; Chen, C. Chem. Commun. 2010, 46, 1127
30. Kawatsura, M.; Kajita, K.; Hayase, S.; Itoh, T. Synlett 2010, 1243
31. Canterbury, D. P.; Frontier, A. J.; Um, J. M.; Cheong, P. H. Y.; Goldfeld, D. A.; Huhn, R. A.; Houk, K. N. Org. Lett. 2008, 10, 4597
32. Canterbury, D. P.; Herrick, I. R.; Um, J.; Houk, K. N.; Frontier, A. J. Tetrahedron 2009, 65, 3165
33. Lehnert, W. Tetrahedron 1972, 28, 663
34. For examples of furan-terminated cationic cyclizations, see: Tanis, S. P.; Herrinton, P. M. J. Org. Chem. 1983, 48, 4572
35. Tanis, S. P.; Herrinton, P. M. J. Org. Chem. 1985, 50, 3988
36. Tanis, S. P.; Herrinton, P. M.; Dixon, L. A. Tetrahedron Lett. 1985, 26, 5347
37. Tanis, S. P.; Chuang, Y. H.; Head, D. B. J. Org. Chem. 1988, 53, 4929
38. Fernandez Mateos, A.; Ferrero Barrueco, O.; Rubio Gonzalez, R. Tetrahedron Lett. 1990, 31, 4343
39. Tanis, S. P.; Dixon, L. A. Tetrahedron Lett. 1987, 28, 2495
40. Childs, R. F.; Shaw, G. S. J. Chem. Soc., Chem. Commun. 1983, 261
41. Childs, R. F.; Diclemente, T.; Lundlucas, E. F.; Richardson, T. J.; Rogerson, C. V. Can. J. Chem. 1983, 61, 856
42. Bergman, J.; Venemalm, L. Tetrahedron Lett. 1987, 28, 3741
43. Lang, Y.; Souza, F. E. S.; Xu, X.; Taylor, N. J.; Assoud, A.; Rodrigo, R. J. Org. Chem. 2009, 74, 5429
44. Hanson, J. R. Nat. Prod. Rep. 1995, 12, 381
45. Steyn, P. S.; Vleggaar, R.; Simpson, T. J. J. Chem. Soc., Chem. Commun. 1984, 765
46. Patre, R. E.; Gawas, S.; Sen, S.; Parameswaran, P. S.; Tilve, S. G. Tetrahedron Lett. 2007, 48, 3517
47. Anderson, E. A.; Alexanian, E. J.; Sorensen, E. J. Angew. Chem., Int. Ed. 2004, 43, 1998