Entropy-controlled supramolecular photochirogenesis: Enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-β-cyclodextrin

Chemical Communications

Volumn , Issue 33, 2005, Pages 4199-4201

  Fukuhara, Gaku ^a   Mori, Tadashi ^a   Wada, Takehiko ^a,b   Inoue, Yoshihisa ^a,c  

^a Department of Molecular Chemistry ^*  (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRIN DERIVATIVE; MONO(6 O BENZOYL)BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; ENTROPY; ISOMERIZATION; METHYLATION; PHOTOCHEMISTRY; PHOTOCHIROGENESIS; PHOTOISOMERIZATION; SUPRAMOLECULAR CHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 25144459418     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b504948b     Document Type: Article

References (22)

1. For reviews, see: (a) H. Rau, Chem. Rev., 1983, 83, 535;
2. (b) Y. Inoue, Chem. Rev., 1992, 92, 741;
3. (c) Y. Inoue and V. Ramamurthy, Chiral Photochemistry, Marcel Dekker, New York, 2004.
4. (a) Y. Inoue, T. Yokoyama, N. Yamasaki and A. Tai, J. Am. Chem. Soc., 1989, 111, 6450;
5. (b) Y. Inoue, N. Yamasaki, T. Yokoyama and A. Tai, J. Org. Chem., 1992, 57, 1332;
6. (c) Y. Inoue, N. Yamasaki, T. Yokoyama and A. Tai, J. Org. Chem., 1993, 58, 1011.
7. (a) Y. Inoue, E. Matsushima and T. Wada, J. Am. Chem. Soc., 1998, 120, 10687;
8. (b) M. Kaneda, S. Asaoka, H. Ikeda, T. Mori, T. Wada and Y. Inoue, Chem. Comm., 2002, 1272;
9. (c) M. Kaneda, A. Nakamura, S. Asaoka, H. Ikeda, T. Mori, T. Wada and Y. Inoue, Org. Biomol. Chem., 2003, 1, 4435.
10. Y. Inoue, H. Ikeda, M. Kaneda, T. Sumimura, S. R. L. Everitt and T. Wada, J. Am. Chem. Soc., 2000, 122, 406.
11. Y. Inoue, T. Wada, S. Asaoka, H. Sato and J.-P. Pete, Chem. Comm., 2000, 251.
12. (a) Y. Inoue, F. Dong, K. Yamamoto, L.-H. Tong, H. Tsuneishi, T. Hakushi and A. Tai, J. Am. Chem. Soc., 1995, 117, 11033;
13. (b) Y. Inoue, T. Wada, N. Sugahara, K. Yamamoto, K. Kimura, L.-H. Tong, X.-M. Gao, Z.-J. Hou and Y. Liu, J. Org. Chem., 2000, 65, 8041.
14. (a) V. Ramamurthy, Chem. Commun., 1998, 1379;
15. (b) A. Joy, R. Scheffer and V. Ramamurthy, Org. Lett, 2000, 2, 119;
16. (c) T. Wada, M. Shikimi, Y. Inoue, G. Lem and N. J. Turro, Chem. Comm., 2001, 1864.
17. (a) T. Yamada, G. Fukuhara and T. Kaneda, Chem. Lett., 2003, 32, 534;
18. (b) R. Nishiyabu and K. Kano, Eur. J. Org. Chem., 2004, 4985.
19. T. Kaneda, T. Fujimoto, J. Goto, K. Asano, Y. Yasufuku, J. H. Jung, C. Hosono and Y. Sakata, Chem. Lett., 2002, 514.
20. (a) S. Asaoka, T. Kitazawa, T. Wada and Y. Inoue, J. Am. Chem. Soc., 1999, 121, 8486;
21. (b) S. Asaoka, T. Wada and Y. Inoue, J. Am. Chem. Soc., 2003, 125, 3008.
22. The host occupancies, determined from circular dichroism spectral titrations upon addition of 1Z to a solution of PMCDbz at 25 °C, were 69% and 90% in 50% and 25% methanol, respectively, while practically no spectral changes were observed in pure methanol.