Asymmetric intramolecular cyclobutane formation via photochemical reaction of N,N-diallyl-2-quinolone-3-carboxamide using a chiral crystalline environment

Organic Letters

Volumn 13, Issue 23, 2011, Pages 6168-6171

  Yagishita, Fumitoshi ^a   Sakamoto, Masami ^a   Mino, Takashi ^a   Fujita, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 82355160811     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2028652     Document Type: Article

References (45)

1. Addadi, L. and Lahav, M. In Origin of Optical Activity in Nature; Walker, D. C., Ed.; Elsevier: New York, 1979; Chapter 14.
2. Green, B. S.; Lahav, M.; Rabinovich, D. Acc. Chem. Res. 1979, 12, 191-197
3. Sakamoto, M. In Chiral Photochemistry; Inoue, Y.; Ramamurthy, V., Eds.; Marcel Dekker: New York, 2004; Vol. 11, pp 415-461.
4. Scheffer, J. R.; Garcia-Garibay, M.; Nalamasu, O. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York and Basel, 1987; Vol. 8, pp 249-338.
5. Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 133-184.
6. Vaida, M.; Popovitz-Bio, R.; Leiserowitz, L.; Lahav, M. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 247-302.
7. Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203-209
8. Sakamoto, M. Chem.-Eur. J. 1997, 3, 684-689
9. Feringa, B. L.; Van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3419-3438
10. Sakamoto, M. J. Photochem. Photobiol. C: Photochem. Rev. 2006, 7, 183-196
11. Elgavi, A.; Green, B. S.; Schmidt, G. M. J. J. Am. Chem. Soc. 1973, 95, 2058-2059
12. van Mil, J.; Addadi, L.; Lahav, M.; Leiserowitz, L. J. Chem. Soc., Chem. Commun. 1982, 584-587
13. Hasegawa, M.; Chung, C. M.; Murro, N.; Maekawa, Y. J. Am. Chem. Soc. 1990, 112, 5676-5677
14. Chung, C. M.; Hasegawa, M. J. Am. Chem. Soc. 1991, 113, 7311-7322
15. Suzuki, T.; Fukushima, T.; Yamashita, Y.; Miyashi, T. J. Am. Chem. Soc. 1994, 116, 2793-2803
16. Zhao, D.; Sun, J.; Ding, K. Chem.-Eur. J. 2004, 10, 5952-5963
17. Hayashi, M.; Hashimoto, Y.; Takezaki, H.; Watanabe, Y.; Saigo, K. Tetrahedron: Asymmetry 1998, 9, 1863-1866
18. Blake, A. J.; Champness, N. R.; Chung, S. S. M.; Li, W. S.; Schroder, M. Chem. Commun. 1997, 1675-1676
19. Fessler, M.; Eller, S.; Bachmann, C.; Gutmann, R.; Trettenbrein, B.; Kopacka, H.; Mueller, T.; Brueggeller, P. Dalton Trans. 2009, 1383-1395
20. Haag, D.; Scharf, H.-D. J. Org. Chem. 1996, 61, 6127-6135
21. Lajiness, J. P.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 13936-13940
22. Sadana, A. K.; Saini, R. K.; Billups, W. E. Chem. Rev. 2003, 103, 1539-1602
23. Sagawa, T.; Takaishi, Y.; Fujimoto, Y.; Duque, C.; Osorio, C.; Ramos, F.; Garzon, C.; Sato, M.; Okamoto, M.; Oshikawa, T.; Ahmed, S. U. J. Nat. Prod. 2005, 68, 502-505
24. Takahashi, M.; Ichikawa, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2005, 46, 57-59
25. Ortuno, R. M.; Moglioni1, A. G.; Moltrasio, G. Y. Curr. Org. Chem. 2005, 9, 237-259
26. Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768
27. Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409-1412
28. Avotins, F. Russ. Chem. Rev. 1993, 62, 897
29. Fülöp, F. Chem. Rev. 2001, 101, 2181
30. Avenoza, A.; Busto, J. H.; Canal, N.; Corzana, F.; Peregrina, J. M.; Fernandez, M. P.; Rodriguez, F. J. Org. Chem. 2010, 75, 545-552
31. Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485-1537
32. Ruff, E. L.; Mladenova, G. Chem. Rev. 2003, 103, 1449-1483
33. Hasegawa, M. Chem. Rev. 1983, 83, 507-518
34. Schlutz, A. G.; Taveras, A. G.; Taylor, R. E.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1992, 114, 8725-8727
35. Toda, F.; Miyamoto, H.; Kikuchi, S. J. Chem. Soc., Chem. Commun. 1995, 621-622
36. Sakamoto, M.; Kato, M.; Oda, E.; Kobaru, S.; Mino, T.; Fujita, T. Tetrahedron 2006, 62, 3028-3032
37. Aoyama, H. J. Chem. Soc., Perkin Trans. 1 1997, 1851-1854
38. Viedma, C. Phys. Rev. Lett. 2005, 94, 065504
39. Pincock, R. E.; Perkins, R. R.; Ma, A. S.; Wilson, K. R. Science 1971, 174, 1018-1020
40. Sakamoto, M.; Utsumi, N.; Ando, M.; Saeki, M.; Mino, T.; Fujita, T.; Katoh, A.; Nishio, T.; Kashima, C. Angew. Chem., Int. Ed. 2003, 42, 4360-4363
41. Sakamoto, M.; Yagishita, F.; Ando, M.; Sasahara, Y.; Kamataki, N.; Ohta, M.; Mino, T.; Kasashima, Y.; Fujita, T. Org. Biomol. Chem. 2010, 8, 5418-5422
42. Cohen, M. D.; Schmidt, G. M. J. J. Chem. Soc. 1964, 1996-2000
43. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647-678
44. Cohen, M. D. Angew. Chem., Int. Ed. Engl. 1975, 14, 386-393
45. Keating, A. E.; Garcia-Garibay, M. A. In Molecular and Supramolecular Photochemistry; Ramamurthy, V.; Schanze, K. S., Eds.; Marcel Dekker: New York, 1998; Vol. 2, pp 195-248.