Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions

Journal of the American Chemical Society

Volumn 133, Issue 37, 2011, Pages 14578-14581

  Burns, Noah Z ^a   Witten, Michael R ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SYSTEM; COOPERATIVE CATALYSIS; CYCLOADDITIONS; DUAL CATALYSIS; ENANTIOSELECTIVE; EXPERIMENTAL EVIDENCE; HIGH ENANTIOSELECTIVITY; ION PAIRS; PYRYLIUM;

CATALYSIS; CYCLOADDITION; THIOUREAS;

ENANTIOSELECTIVITY;

HYDROXYACID; OXIDOPYRYLIUM; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS LINKING; CYCLOADDITION; ENANTIOSELECTIVITY;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, BRIDGED-RING; STEREOISOMERISM; THIOUREA;

EID: 80052798187     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja206997e     Document Type: Article

References (56)

1. Singh, V.; Krishna, U. M.; Vikrant; Trivedi, G. K. Tetrahedron 2008, 64, 3405-3428
2. Pellissier, H. Adv. Synth. Catal. 2011, 353, 189-218
3. Ratnayake, R.; Covell, D.; Ransom, T. T.; Gustafson, K. R.; Beutler, J. A. Org. Lett. 2009, 11, 57-60
4. Marrero, J.; Rodríguez, A. D.; Barnes, C. L. Org. Lett. 2005, 7, 1877-1880
5. Uchiyama, N.; Kiuchi, F.; Ito, M.; Honda, G.; Takeda, Y.; Khodzhimatov, O. K.; Ashurmetov, O. A. J. Nat. Prod. 2003, 66, 128-131
6. Sun, K.; Li, X.; Li, W.; Wang, J.; Liu, J.; Sha, Y. Chem. Pharm. Bull. 2004, 52, 1483-1486
7. Yin, H.-B.; He, Z.-S.; Ye, Y. J. Nat. Prod. 2000, 63, 1164-1165
8. Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957
9. Bromidge, S. M.; Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1985, 1725-1730
10. Fishwick, C. W. G.; Mitchell, G.; Pang, P. F. W. Synlett 2005, 285-286
11. Krishna, U. M. Tetrahedron Lett. 2010, 51, 2148-2150
12. Yadav, A. A.; Sarang, P. S.; Trivedi, G. K.; Salunkhe, M. M. Synlett 2007, 989-991
13. Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958
14. Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977
15. Ali, M. A.; Bhogal, N.; Findlay, J. B. C.; Fishwick, C. W. G. J. Med. Chem. 2005, 48, 5655-5658
16. Roethle, P. A.; Hernandez, P. T.; Trauner, D. Org. Lett. 2006, 8, 5901-5904
17. Li, Y.; Nawrat, C. C.; Pattenden, G.; Winne, J. M. Org. Biomol. Chem. 2009, 7, 639-640
18. Nicolaou, K. C.; Kang, Q.; Ng, S. Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 8219-8222
19. Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898
20. López, F.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2000, 2, 1005-1007
21. López, F.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3683-3685
22. Wender, P. A.; Bi, F. C.; Buschmann, N.; Gosselin, F.; Kan, C.; Kee, J.-M.; Ohmura, H. Org. Lett. 2006, 8, 5373-5376
23. Garnier, E.C.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 7449-7458
24. Hodgson, D. M.; Stupple, P. A.; Johnstone, C. ARKIVOC 2003, vii) 49-58
25. Kitagaki, S.; Anada, M.; Kataoka, O.; Matsuno, K.; Umeda, C.; Watanabe, N.; Hashimoto, S. J. Am. Chem. Soc. 1999, 121, 1417-1418
26. Hodgson, D. M.; Labande, A. H.; Pierard, F. Y. T. M.; Expósito Castro, M. A. J. Org. Chem. 2003, 68, 6153-6159
27. Hodgson, D. M.; Brückl, T.; Glen, R.; Labande, A. H.; Selden, D. A.; Dossetter, A. G.; Redgrave, A. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5450-5454
28. Shimada, N.; Anada, M.; Nakamura, S.; Nambu, H.; Tsutsui, H.; Hashimoto, S. Org. Lett. 2008, 10, 3603-3606
29. Ishida, K.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2010, 132, 8842-8843
30. Marcoux, D.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2009, 131, 6970-6972
31. Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404-13405
32. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198-7199
33. Klausen, R. S.; Jacobsen, E. N. Org. Lett. 2009, 11, 887-890
34. Zuend, S. J.; Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 15358-15374
35. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986-990
36. Knowles, R. R.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030-5032
37. Brown, A. R.; Kuo, W.-H.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286-9288
38. De, C. K.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 17060-17061
39. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187-1198
40. Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359-3361
41. Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1982, 1056-1057
42. Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261-1265
43. Sammes, P. G.; Street, L. J. J. Chem. Res., Synop. 1984, 196-197
44. Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217-220
45. Wittkopp, A.; Schreiner, P. R. Chem. Eur. J. 2003, 9, 407-414
46. McDaniel, D. H.; Brown, H. C. J. Org. Chem. 1958, 23, 420-427
47. Reis, Ö.; Eymur, S.; Reis, B.; Demir, A. S. Chem. Commun. 2009, 1088-1090
48. Companyó, X.; Valero, G.; Crovetto, L.; Moyano, A.; Rios, R. Chem. Eur. J. 2009, 15, 6564-6568
49. Demir, A. S.; Eymur, S. Tetrahedron: Asymmetry 2010, 21, 112-115
50. Demir, A. S.; Eymur, S. Tetrahedron: Asymmetry 2010, 21, 405-409
51. Bordwell, F. G.; Algrim, D. J.; Harrelson, J. A., Jr. J. Am. Chem. Soc. 1988, 110, 5903-5904
52. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672-12673
53. Zhang, G.; Musgrave, C. B. J. Phys. Chem. A 2007, 111, 1554-1561
54. López, F.; Castedo, L.; Mascareñas, J. L. J. Org. Chem. 2003, 68, 9780-9786
55. Wang, S. C.; Tantillo, D. J. J. Org. Chem. 2008, 73, 1516-1523
56. Legault, C. Y., CYLview, version 1.0b; Université de Sherbrooke, 2009; http://www.cylview.org.