Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by aroyl-β-cyclodextrins: A critical enantioselectivity control by substituents

Journal of Organic Chemistry

Volumn 73, Issue 19, 2008, Pages 7695-7701

  Lu, Runhua ^a,b   Yang, Cheng ^c   Cao, Yujuan ^d   Tong, Linhui ^e   Jiao, Wei ^b   Wada, Takehiko ^c   Wang, Zhizhong ^b   Mori, Tadashi ^d   Inoue, Yoshihisa ^c  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c OSAKA UNIVERSITY   (Japan)

^d SOUTH CHINA NORMAL UNIVERSITY   (China)

^e LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; CHLORINE COMPOUNDS; CYCLODEXTRINS; ENANTIOSELECTIVITY;

CHEMICAL EQUATIONS; COMPLEX STABILITY; CYCLODEXTRINS (CDS); CYCLOOCTENE; METHOXY;

ISOMERIZATION;

BENZOIC ACID; BETA CYCLODEXTRIN DERIVATIVE; CARBONYL DERIVATIVE; METHANOL;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; ISOMERIZATION; PHOTOSENSITIZATION; SYNTHESIS;

BETA-CYCLODEXTRINS; CYCLOOCTANES; METHANOL; OPTICAL ROTATION; PHOTOCHEMISTRY; SOLUTIONS; STEREOISOMERISM;

EID: 53049101373     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801439n     Document Type: Article

References (32)

1. (a) Inoue, Y. Chem. Rev. 1992, 92, 741.
2. (b) Inoue, Y.; Ramamurthy, V. Chiral Photochemistry; Marcel Dekker: New York, 2004.
3. (c) Yang, C.; Fukuhara, G.; Nakamura, A.; Origane, Y.; Fujita, K.; Yuan, D.-Q.; Mori, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol. A: Chem. 2005, 173, 375.
4. (d) Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2005, 4199.
5. (e) Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 8233.
6. (f) Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 966.
7. Everitt S. R. L.; Inoue, Y. In Organic Molecular Photochemistry, Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York, 1999; p 71.
8. (a) Inoue, Y.; Dong, F.; Yamamoto, K.; Tong, L.-H.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1995, 117, 11033.
9. (b) Sugahara, N.; Kawano, M.; Wada, T.; Inoue, Y. Nucleic Acids Symp. Ser. 2000, 44, 115.
10. (c) 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.
11. (d) Gao, Y.-Y.; Inoue, M.; Wada, T.; Inoue, Y. J Incl. Phenom. Macrocycl. Chem. 2004, 50, 111.
12. (e) Tong, L.-H.; Lu, R. H.; Inoue, Y. Prog. Chem. 2006, 18, 533.
13. Chong, K.-C.-W.; Sivaguru, J.; Shichi, T.; Yoshimi, Y.; Ramamurthy, V.; Scheffer, J.-R. J. Am. Chem. Soc. 2002, 124, 2858.
14. (a) Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982.
15. (b) Grosch, B.; Orlebar, C.-N.; Herdtweck, E.; Kaneda, M.; Wada, T.; Inoue, Y.; Bach, T. Chem. Eur. J. 2004, 10, 2179.
16. (a) Rao, V.-P.; Turro, N.-J. Tetrahedron Lett. 1989, 30, 4641.
17. (b) Koodanjeri, S.; Joy, A.; Ramamurthy, V. Tetrahedron 2000, 56, 7003.
18. (c) Shailaja, J.; Karthikeyan, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9335.
19. (d) Koodanjeri, S.; Joy, A.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9229.
20. (e) Vizvardi, K.; Desmt, K.; Luyten, I.; Sandra, P.; Hoornaert, G.; Eycken, V. E. Org. Lett. 2001, 3, 1173.
21. (a) Zandomeneghi, M. J. Am. Chem. Soc. 1991, 113, 7774.
22. (b) Lhiaubet-Vallet, V.; Sarabia, Z.; Bosca, F.; Miranda, M. A. J. Am. Chem. Soc. 2004, 126, 9538.
23. (c) Wada, T.; Nishijima, M.; Fujisawa, T.; Sugahara, N.; Mori, T.; Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 7492.
24. Wada, T.; Sugahara, N.; Kawano, M.; Inoue, Y. Chem. Lett. 2000, 1174.
25. (a) Takahashi, K. Chem. Rev. 1998, 98, 2013.
26. (b) Breslow, R.; Dong, S. Chem. Rev. 1998, 98, 1997.
27. Yang, C.; Mori, T.; Wada, T.; Inoue, Y. New J. Chem. 2007, 31, 697.
28. Lu, R.; Yang, C.; Cao, Y.; Wang, Z.; Wada, T.; Jiao, W.; Mori, T.; Inoue, Y. Chem. Commun. 2008, 3, 374-376.
29. Kajtar, M.; Horvath-Toro, C.; Kuthi, E.; Szejtli, J. Acta Chim. Acad. Sci. Hung 1982, 110, 327.
30. Tong, L.-H.; Hou, Z.-J.; Inoue, Y.; Tai, A. J. Chem. Soc., Perkin Trans. 2 1992, 1253.
31. Inoue, Y.; Yamamoto, K.; Wada, T.; Everitt, S.; Gao, X.-M.; Hou, Z.-J.; Tong, L.-H.; Jiang, S.-K.; Wu, H.-M. J. Chem. Soc., Perkin Trans. 2 1998, 1807.
32. Tong, L. H. Inclusion Complextion and Photosensitization of Cyclooctene with β-Cyclodextrin 6-O-Benzeate. In Final Rep. Inoue Photochirogenesis Project (ERATO, JST) 2001, 8, 13.