Enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate catalyzed by 6A,6X -diamino-6A,6X-dideoxy-γ-cyclodextrins: Manipulation of product chirality by electrostatic interaction, temperature and solvent in supramolecular photochirogenesis

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 173, Issue 3 SPEC. ISS., 2005, Pages 375-383

  Yang, Cheng ^a   Fukuhara, Gaku ^b   Nakamura, Asao ^a   Origane, Yumi ^a   Fujita, Kahee ^c   Yuan, De Qi ^c   Mori, Tadashi ^b   Wada, Takehiko ^b   Inoue, Yoshihisa ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c NAGASAKI UNIVERSITY   (Japan)

Author keywords

Anthracenecarboxylic acid; Chirality inversion; Diamino cyclodextrin; Enantiodifferentiation; Enthalpy entropy compensation; Photocyclodimerization

Indexed keywords

EID: 21644487643     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2005.04.017     Document Type: Article

References (35)

1. Y. Inoue V. Ramamurthy (Eds.), Chiral Photochemistry 2004 Marcel Dekker
2. Y. Inoue Chem. Rev. 92 1992 741
3. H. Rau Chem. Rev. 83 1983 535
4. K.C.W. Chong J. Sivaguru T. Shichi Y. Yoshimi V. Ramamurthy J.R. Scheffer J. Am. Chem. Soc. 124 2002 2858
5. T. Bach H. Bergmann B. Grosch K. Harms J. Am. Chem. Soc. 124 2002 7982
6. B. Grosch C.N. Orlebar E. Herdtweck M. Kaneda T. Wada Y. Inoue T. Bach Chem. Eur. J. 10 2004 2179
7. V.P. Rao N.J. Turro Tetrahedron Lett. 30 1989 4641
8. S. Koodanjeri A. Joy V. Ramamurthy Tetrahedron 56 2000 7003
9. J. Shailaja S. Karthikeyan V. Ramamurthy Tetrahedron Lett. 43 2002 9335
10. S. Koodanjeri A. Joy V. Ramamurthy Tetrahedron Lett. 43 2002 9229
11. Y. Inoue T. Wada N. Sugahara K. Yamamoto K. Kimura L.H. Tong X.M. Gao Z. Hou Y. Liu J. Org. Chem. 65 2000 8041
12. Y. Inoue F. Dong K. Yamamoto L.H. Tong H. Tsuneishi T. Hakushi A. Tai J. Am. Chem. Soc. 117 1995 11033
13. K. Vizvardi K. Desmt I. Luyten P. Sandra G. Hoornaert V.E. Eycken Org. Lett. 3 2001 1173
14. M. Zandomeneghi J. Am. Chem. Soc. 113 1991 7774
15. V. Lhiaubet-Vallet Z. Sarabia F. Bosca M.A. Miranda J. Am. Chem. Soc. 126 2004 9538
16. T. Wada N. Sugahara M. Kawano Y. Inoue Chem. Lett. 2000 1174
17. K. Takahashi Chem. Rev. 98 1998 2013
18. R. Breslow S. Dong Chem. Rev. 98 1998 1997
19. A. Nakamura Y. Inoue J. Am. Chem. Soc. 125 2003 966
20. T. Wada M. Nishijima T. Fujisawa N. Sugahara T. Mori A. Nakamura Y. Inoue J. Am. Chem. Soc. 125 2003 7492
21. T. Tamaki T. Kokubu J. Inclusion Phenom. 2 1984 815
22. T. Tamaki T. Kokubu K. Ichimura Tetrahedron 43 1987 1485
23. H. Ikeda T. Nihei A. Ueno J. Org. Chem. 70 2005 1237
24. J.N. Moorthy K. Venkatesan R.G. Weiss J. Org. Chem. 57 1992 3292
25. W. Herrmann S. Wehrle G. Wenz J. Chem. Soc. Chem. Commun. 1997 1709
26. T. Utsuki F. Hirayama K. Uekema J. Chem Soc. Perkin Trans. 2 1993 109
27. M.V. Rekharsky Y. Inoue Chem. Rev. 98 1998 1875
28. K. Fujita H. Yamamura T. Imoto T. Fujioka K. Mihashi J. Org. Chem. 53 1988 1943
29. Y. Inoue H. Ikeda M. Kaneda T. Sumimura S.R.L. Everitt T. Wada J. Am. Chem. Soc. 122 2000 406
30. Y. Gao M. Inoue T. Wada Y. Inoue J. Incl. Phenom. Macrocycl. Chem. 50 2004 111
31. Y. Inoue T. Wada S. Asaoka H. Sato J.P. Pete Chem. Commun. 1999 251
32. Y. Inoue N. Sugahara T. Wada Pure Appl. Chem. 73 2001 475
33. Y. Inoue T. Yokoyama N. Yamasaki A. Tai Nature 341 1989 225
34. R. Hoffmann Y. Inoue J. Am. Chem. Soc. 121 1999 10702
35. S. Asaoka T. Kitazawa T. Wada Y. Inoue J. Am. Chem. Soc. 121 1999 8486