Selective approach toward multifunctionalized lactams by lewis acid promoted PhSe group transfer radical cyclization

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3232-3239

  Yu, Jin Di ^a   Ding, Wei ^a   Lian, Gao Yan ^a   Song, Ke Sheng ^b   Zhang, Dan Wei ^a   Gao, Xiang ^a   Yang, Dan ^a,b  

^a FUDAN UNIVERSITY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION PRODUCTS; ENAMIDES; GROUP TRANSFER; LEWIS ACID; NITROGEN HETEROCYCLES; RADICAL CYCLIZATIONS; REGIOSPECIFIC; RING CLOSURES; STEREO-SELECTIVE; UV IRRADIATION;

ACIDS; AMIDES; ESTERS; SUBSTRATES; YTTERBIUM;

CYCLIZATION;

ALPHA PHENYLSELENO AMIDO ESTER; ESTER; LACTAM; LEWIS ACID; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; ULTRAVIOLET IRRADIATION;

CYCLIZATION; FREE RADICALS; LACTAMS; MESYLATES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOSELENIUM COMPOUNDS; STEREOISOMERISM; ULTRAVIOLET RAYS;

EID: 77952537954     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100139u     Document Type: Article

References (72)

1. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355
2. Masse, C. E.; Morgan, A. J.; Adams, J.; Panek, J. S. Eur. J. Org. Chem. 2000, 2513
3. Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1
4. Rosensiel, P. V. Neurotherapeutics 2007, 4, 84
5. Griswold, D. E.; Webb, E. F.; Breton, J.; White, J. R.; Marshall, P. J.; Torphy, T. J. Inflammation 1997, 17, 333
6. Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chiou, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039
7. Kibayashi, C. Chem. Pharm. Bull. 2005, 53, 1375
8. El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Synthesis 2004, 2249
9. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986.
10. Curran, D. P. Synthesis 1988, 417-489
11. Malacria, M. Chem. Rev. 1996, 96, 289
12. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163
13. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991
14. Renaud, P.; Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol. 2.
15. Zhang, W. Tetrahedron 2001, 57, 7237
16. McCarrol, A. J.; Walton, J. C. Angew. Chem., Int. Ed. 2001, 40, 2224
17. Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 695
18. Bowman, W. R.; Fletcher, A. J.; Potts, G. B. S. J. Chem. Soc., Perkin Trans. 1 2002, 2747
19. Rheault, T. R.; Sibi, M. P. Synthesis 2003, 803
20. Ishibashi, H. Chem. Record 2006, 6, 23
21. Majumdar, K. C.; Basu, P. K.; Chattopadhyay, S. K. Tetrahedron 2007, 63, 793
22. Uenoyama, Y.; Fukuyama, T.; Ryu, I. Org. Lett. 2007, 9, 935
23. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140
24. Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1989, 111, 6265
25. Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872
26. Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041
27. Jolly, R. S.; Livinghouse, J. Am. Chem. Soc. 1988, 110, 7536.
28. De Buyck, L.; Cagnoli, R.; Ghelfi, F.; Merighi, G.; Mucci, A.; Pagnoni, U. M.; Parsons, A. F. Synthesis 2004, 1680
29. Helliwell, M.; Fengas, D.; Knight, C. K.; Parker, J.; Quayle, P.; Raftery, J.; Richards, S. N. Tetrahedron Lett. 2005, 46, 7129
30. Chapelon, A.-S.; Ollivier, C.; Santelli, M. Tetrahedron Lett. 2006, 47, 2747
31. Edlin, C. D.; Faulkner, J.; Helliwell, M.; Knight, C. K.; Parker, J.; Quayle, P.; Raftery, J. Tetrahedron 2006, 62, 3004
32. Yang., D.; Gu, S.; Yan, Y.-L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612
33. Yang, D.; Gu, S.; Yan, Y.-L.; Zhao, H.-W.; Zhu, N.-Y. Angew. Chem., Int. Ed. 2002, 41, 3014
34. Yang., D.; Zheng, B.-F.; Gao, Q.; Gu, S.; Zhu, N.-Y. Angew. Chem., Int. Ed. 2006, 45, 255
35. Yang, D; Lian, G.-Y.; Yang, H.-F.; Yu, J.-D.; Zhang, D.-W.; Gao, X. J. Org. Chem. 2009, 74, 8610-8615
36. Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746
37. Musa, O. M.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 1022
38. Mahalingam, A. K.; Wu, X.; Alterman, M. Tetrahedron Lett. 2006, 47, 3051
39. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227
40. Tsuruta, H.; Yamaguchi, K.; Imamoto, T. Chem. Commun. 1999, 1703
41. For the improvement of stereoselectivity in some free-radical transformations by magnesium-based Lewis acids, see: Guérin, B.; Ogilvie, W. W.; Guindon, Y. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; and references cited therein.
42. Dakterniuks, D.; Perchyonok, V. T.; Schiesser, C. H. Tetrahedron: Asymmetry 2003, 14, 3057
43. For details, see the Supporting Information.
44. Yang, D.; Gao, Q.; Zheng, B.-F.; Zhu, N.-Y. J. Org. Chem. 2004, 69, 8821
45. Krapcho, A. P. ARKIVOC 2007, 1
46. Krapcho, A. P. ARKIVOC 2007, 54
47. Kammerer, C.; Prestat, G.; Madec, D.; Poli, G. Chem.-Eur. J. 2009, 15, 4224
48. Yang, D.; Gao, Q.; Lee, O.-Y. Org. Lett. 2002, 4, 1239
49. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734
50. Julia, M. Acc. Chem. Res. 1971, 4, 386 and references cited therein.
51. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482
52. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925
53. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959
54. Padwa, A.; Nimmesgern, H.; Wong, G. S. K. Tetrahedron Lett. 1985, 26, 957
55. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564
56. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741
57. Villar, F.; Kolly-Kovac, T.; Equey, O.; Renaud, P. Chem.-Eur. J. 2003, 9, 1566
58. Corminboeuf, O.; Renaud, P.; Schiesser, C. H. Chem.-Eur. J. 2003, 9, 1578
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B05; Gaussian, Inc.: Pittsburgh, PA, 2003.
60. Cances, M. T.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
61. Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253
62. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151
63. Cossi, M.; Scalmani, G..; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43
64. Pearson, W. H.; Lian, B. W. Angew. Chem., Int. Ed. 1998, 37, 1724
65. Overman, L. E.; Shim, J. J. Org. Chem. 1993, 58, 4662
66. Campos, K. R.; Journet, M.; Lee, S.; Grabowski, E. J. J.; Tillyer, R. D. J. Org. Chem. 2005, 70, 268
67. Ozawa, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2000, 2, 2955
68. Ishibashi, H.; Sato, T.; Ikeda, M. Synthesis 2002, 6, 695 and references cited therein.
69. DAnnibale, A.; Nanni, D.; Trogolo, C.; Umani, F. Org. Lett. 2000, 2, 401
70. Edmonds, D. J.; Muir, K. W.; Procter, D. J. J. Org. Chem. 2003, 68, 3190
71. Clark, A. J.; Battle, G. M.; Bridge, A. Tetrahedron Lett. 2001, 42, 4409
72. Chatgilialoglu, C.; Ferreri, C.; Guerra, M.; Timokhin, V.; Froudakis, G.; Gimisis, T. J. Am. Chem. Soc. 2002, 124, 10765