Pressure and temperature-controlled enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate mediated by secondary face- and skeleton-modified γ-cyclodextrins

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3126-3136

  Yang, Cheng ^a   Nakamura, Asao ^a   Fukuhara, Gaku ^b   Origane, Yumi ^a   Mori, Tadashi ^b   Wada, Takehiko ^b   Inoue, Yoshihisa ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; CHEMICAL MODIFICATION; DIMERS; PRESSURE CONTROL; TEMPERATURE CONTROL;

CYCLODEXTRINS; PHOTOCYCLODIMERIZATION; SUPRAMOLECULAR PHOTOCHIROGENIC REACTION;

ORGANIC COMPOUNDS;

2 ANTHROIC ACID; CARBOXYLIC ACID DERIVATIVE; GAMMA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DIMERIZATION; ENANTIOMER; ENANTIOSELECTIVITY; LOW TEMPERATURE; PHOTOCYCLODIMERIZATION; PRESSURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; TEMPERATURE SENSITIVITY;

EID: 33645792786     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0601718     Document Type: Article

References (85)

1. Inoue, Y.; Ramamurthy, V. Chiral Photochemistry; Marcel Dekker: New York, 2004.
2. Inoue, Y. Chem. Rev. 1992, 92, 741.
3. Rau, H. Chem. Rev. 1983, 83, 535.
4. Everitt, S. R. S.; Inoue, Y. Organic Molecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 1999; Vol. 3.
5. Inoue, Y.; Sugahara, N.; Wada, T. Pure Appl. Chem. 2001, 73, 475.
6. Inoue, Y.; Wada, T.; Asaoka, S.; Sato, H.; Pete, J.-P. Chem. Commun. 2000, 251.
7. Inoue, Y.; Okano, T.; Yamasaki, N.; Tai, A. J. Photochem. Photobiol., A 1992, 61.
8. Nishiyama, Y.; Kaneda, M.; Saito, R.; Mori, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 2004, 126, 6568.
9. Kaneda, M.; Nishiyama, Y.; Asaoka, S.; Mori, T.; Wada, T.; Inoue, Y. Org. Biomol. Chem. 2004, 2, 1295.
10. Asaoka, S.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 3008.
11. Asaoka, S.; Horiguchi, H.; Wada, T.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 2000, 737.
12. Lhiaubet-Vallet, V.; Sarabia, Z.; Bosca, F.; Miranda, M. A. J. Am. Chem. Soc. 2004, 126, 9538.
13. Chong, K. C.; Sivaguru, J.; Shichi, T.; Yoshimi, Y.; Ramamurthy, V.; Scheffer, J. R. J. Am. Chem. Soc. 2002, 124, 2858.
14. Joy, A.; Ramamurthy, V. Chemistry 2000, 6, 1287.
15. Sivaguru, J.; Sunoj, R. B.; Wada, T.; Origane, Y.; Inoue, Y.; Ramamurthy, V. J. Org. Chem. 2004, 69, 6533.
16. Wada, T.; Shikimi, M.; Inoue, Y.; Lem, G.; Turro, N. J. Chem. Commun. 2001, 1864.
17. Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982.
18. Aechtner, T.; Dressel, M.; Bach, T. Angew. Chem., Int. Ed. 2004, 43, 5849.
19. Bach, T.; Bergmann, H.; Brummerhop, H.; Lewis, W.; Harms, K. Chemistry 2001, 7, 4512.
20. Bauer, A.; Weskamper, F.; Grimme, S.; Bach, T. Nature 2005, 1139.
21. Inoue, Y. Nature 2005, 1099.
22. Wada, T.; Nishijima, M.; Fujisawa, T.; Sugahara, N.; Mori, T.; Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 7492.
23. Sugahara, N.; Kawano, M.; Wada, T.; Inoue, Y. Nucleic Acids Symp. Ser. 2000, 115.
24. Gao, Y.; Wada, T.; Yang, K.; Kim, K.; Inoue, Y. Chirality 2005, 17, 19.
25. Inoue, Y.; Wada, T.; Sugahara, N.; Yamamoto, K.; Kimura, K.; Tong, L.-H.; Gao, X.-M.; Hou, Z.-J.; Liu, Y. J. Org. Chem. 2000, 65, 8041.
26. Inoue, Y.; Dong, S. F.; Yamamoto, K.; Tong, L.-H.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1995, 113, 2793.
27. Gao, Y.; Inoue, M.; Wada, T.; Inoue, Y. J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 111.
28. Inoue, Y.; Kosaka, S.; Matsumoto, K.; Tsuneishi, H.; Hakushi, T.; Tai, A.; Nakagawa, K.; Tong, L. J. Photochem. Photobiol., A 1993, 71, 61.
29. Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 966.
30. Yang, C.; Fukuhara, G.; Nakamura, A.; Origane, Y.; Fujita, K.; Yuan, D.-Q.; Mori, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol., A 2005, 173, 375.
31. Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2005, 127, 5338.
32. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
33. Takahashi, K. Chem. Rev. 1998, 98, 2013.
34. Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529.
35. Ortega-Caballero, F.; Rousseau, C.; Christensen, B.; Petersen, T. E.; Bols, M. J. Am. Chem. Soc. 2005, 127, 3238.
36. Kano, K.; Nishiyabu, R.; Yamazaki, T.; Yamazaki, I. J. Am. Chem. Soc. 2003, 125, 10625.
37. Liu, Y.; Wang, H.; Chen, Y.; Ke, C. F.; Liu, M. J. Am. Chem. Soc. 2005, 127, 657.
38. Rao, V. P.; Turro, N. J. Tetrahedron Lett. 1989, 30, 4641.
39. Koodanjeri, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9229.
40. Tamaki, T.; Kokubu, T.; Ichimura, K. Tetrahedron Lett. 1987, 43, 1485.
41. Tamaki, T.; Kokubu, T. J. Inclusion Phenom. Macrocyclic Chem. 1984, 2, 815.
42. Ikeda, H.; Nihei, T.; Ueno, A. J. Org. Chem. 2005, 70, 1237.
43. Herrmann, W.; Wehrle, S.; Wenz, G. Chem. Commun. 1997, 1709.
44. Rao, K. S.; Hubig, S. M.; Moorthy, J. N.; Kochi, J. K. J. Org. Chem. 1999, 64, 8098.
45. Banu, H. S.; Lalitha, A.; Pitchumani, K.; Srinivasan, C. Chem. Commun. 1999, 607.
46. Brett, T. J.; Alexander, J. M.; Stezowski, J. J. J. Chem. Soc., Perkin Trans. 2 2000, 1105.
47. Brett, T. J.; Alexander, J. M.; Stezowski, J. J. J. Chem. Soc., Perkin Trans. 2 2000, 1095.
48. Moorthy, J. N.; Venkatesan, K.; Weiss, R. G. J. Org. Chem. 1992, 57, 3292.
49. Koodanjeri, S.; Joy, A.; Ramamurthy, V. Tetrahedron 2000, 56, 7003.
50. Shailaja, J.; Karthikeyan, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9335.
51. Vizvardi, K.; Desmet, K.; Luyten, I.; Sandra, P.; Hoornaert, G.; Van der Eycken, E. Org. Lett. 2001, 3, 1173.
52. Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2005, 4199.
53. Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977.
54. Breslow, R.; Czarnik, A. J. Am. Chem. Soc. 1983, 105, 1390.
55. Fujita, K.; Chen, W.-H.; Yuan, D.-Q.; Nogami, Y.; Koga, T.; Fujioka, T.; Mihashi, K.; Immel, S.; Lichtenthaler, F. W. Tetrahedron: Asymmetry 1999, 10, 1689.
56. Fujita, K.; Okabe, Y.; Ohta, K.; Yamamura, H.; Tahara, T.; Nogami, Y.; Koga, T. Tetrahedron Lett. 1996, 37, 1825.
57. Chen, W.-H.; Fukudome, M.; Yuan, D.-Q.; Fujioka, T.; Mihashi, K.; Fujita, K. Chem. Commun. 2000, 541.
58. Yuan, D.-Q.; Tahara, T.; Chen, W.-H.; Okabe, Y.; Yang, C.; Yagi, Y.; Nogami, Y.; Fukudome, M.; Fujita, K. J. Org. Chem. 2003, 68, 9456.
59. Lichtenthaler, F. W.; Mondel, S. Carbohydr. Res. 1997, 303, 293.
60. See Supporting Information for UV-vis and CD spectral analysis.
61. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy Exciton Coupling in Organic Stereochemistry; University Science Books: Sausalito, CA, 1983.
62. Chan, I. Y.; Huzeifa, I.; Prass, B.; Stehlik, D. J. Chem. Phys. 2002, 117, 4419.
63. Chung, W. S.; Turro, N. J.; Mertes, J.; Mattay, J. J. Org. Chem. 1989, 54, 4881.
64. Hara, K.; Bulgarevich, D. S.; Kajimoto, O. J. Chem. Phys. 1996, 104, 9431.
65. Crane, D. R.; Ford, P. C. J. Am. Chem. Soc. 1991, 113, 8510.
66. Schneider, S.; Jager, W. J. Phys. Chem. 1996, 100, 8118.
67. Hara, K.; Ito, N.; Kajimoto, O. J. Phys. Chem. A 1997, 101, 2240.
68. Kaneda, M.; Asaoka, S.; Ikeda, H.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2002, 1272.
69. Mori, T.; Weiss, R. G.; Inoue, Y. J. Am. Chem. Soc. 2004, 126, 8961.
70. Saito, H.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2004, 1652.
71. Turro, N. J.; Okubo, T.; Weed, G. C. Photochem. Photobiol. 1982, 35, 325.
72. Sueishi, Y.; Tobisako, H.; Kotake, Y. J. Phys. Chem. B 2004, 108, 12623.
73. Abou-Hamdan, A.; Bugnon, P.; Saudan, C.; Lye, P. G.; Merbach, A. E. J. Am. Chem. Soc. 2000, 122, 592.
74. Inoue, Y.; Matsushima, E.; Wada, T. J. Am. Chem. Soc. 1998, 120, 10687.
75. Hoffmann, R.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 10702.
76. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
77. Rekharsky, M. V.; Inoue, Y. J. Am. Chem. Soc. 2002, 124, 12361.
78. Liu, Y.; Han, B.-H.; Li, B.; Zhang, Y.-M.; Zhao, P.; Chen, Y.-T.; Wada, T.; Inoue, Y. J. Org. Chem. 1998, 63, 1444.
79. Harries, D.; Rau, D. C.; Parsegian, V. A. J. Am. Chem. Soc. 2005, 127, 2184.
80. Rong, D.; D'Souza, V. T. Tetrahedron Lett. 1990, 31, 4275.
81. Ueno, A.; Breslow, R. Tetrahedron Lett. 1982, 23, 3451.
82. Fujita, K.; Tahara, T.; Koga, T. Chem. Lett. 1989, 821.
83. Yang, C.; Yuan, D.-Q.; Nogami, Y.; Fujita, K. Tetrahedron Lett. 2003, 44, 4641.
84. Fujita, K.; Ohta, K.; Ikegami, Y.; Shimada, H.; Tahara, T.; Nogami, Y.; Koga, T.; Saito, K.; Nakajima, T. Tetrahedron Lett. 1994, 35, 9577.
85. Hamasaki, K.; Ikeda, H.; Nakamura, A.; Ueno, A.; Toda, A.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1993, 115, 5035.