Diastereodifferentiating photocyclodimerization of 2-anthracenecarboxylate tethered to cellulose scaffold

Journal of Organic Chemistry

Volumn 75, Issue 12, 2010, Pages 4307-4310

  Fukuhara, Gaku ^a   Nakamura, Tomohiro ^a   Yang, Cheng ^a   Mori, Tadashi ^a   Inoue, Yoshihisa ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL CHANGE; CRITICAL FUNCTIONS; DEGREES OF SUBSTITUTION; ENANTIOMERIC EXCESS; FLEXIBLE POLYMERS; PHOTO-IRRADIATION; PHOTOCYCLODIMERIZATION; PRODUCT DISTRIBUTIONS;

DISTRIBUTION FUNCTIONS;

2 ANTHROIC ACID; CARBOXYLIC ACID; CELLULOSE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DIMERIZATION; PHOTOCYCLODIMERIZATION; SAPONIFICATION; SUBSTITUTION REACTION;

ANTHRACENES; CARBOXYLIC ACIDS; CELLULOSE; CYCLIZATION; DIMERIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; STEREOISOMERISM;

EID: 77953521872     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100596n     Document Type: Article

References (24)

1. For reviews, see: Griesbeck, A. G.; Meierhenrich, U. J. Angew. Chem., Int. Ed. 2002, 41, 3147
2. Inoue, Y.; Ramamurthy, V., Eds. Chiral Photochemistry; Marcel Dekker: New York, 2004.
3. Müller, C.; Bach, T. Aust. J. Chem. 2008, 61, 557
4. Hoffmann, N. Chem. Rev. 2008, 108, 1052
5. Nobel Lectures. See: Knowles, W. S. Angew. Chem., Int. Ed. 2002, 41, 1998
6. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008
7. Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2024
8. Hammond, G. S.; Cole, R. S. J. Am. Chem. Soc. 1965, 87, 3256
9. Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982
10. Albrecht, D.; Vogt, F.; Bach, T. Chem. - Eur. J. 2010, 16, 4284
11. Inoue, Y.; Wada, T.; Asaoka, S.; Sato, H.; Pete, J.-P. Chem. Commun. 2000, 251
12. Tamaki, T.; Kokubu, T.; Ichimura, K. Tetrahedron 1987, 43, 1485
13. Yang, C.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 5786
14. Nishijima, M.; Wada, T.; Mori, T.; Pace, T. C. S.; Bohne, C.; Inoue, Y. J. Am. Chem. Soc. 2007, 129, 3478
15. Yang, C.; Mori, T.; Origane, Y.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. J. Am. Chem. Soc. 2008, 130, 8574
16. See: Cellulose and Cellulose Derivatives Special Issue. Macromol. Chem. Phys. 2000, 201, 1913.
17. See: Cyclodextrins Special Issue. Chem. Rev. 1998, 98, 1741.
18. Redl, F. X.; Lutz, M.; Daub, J. Chem. - Eur. J. 2001, 7, 5350
19. Takeuchi, M.; Chin, Y.; Imada, T.; Shinkai, S. Chem. Commun. 1996, 1867
20. Berova, N.; Bari, L. D.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914
21. For recent examples, see: Ide, N.; Tsuji, Y.; Fukuda, T.; Miyamoto, T. Macromolecules 1996, 29, 3851
22. Yamaguchi, J.; Watanabe, J.; Takai, M.; Ishihara, K. J. Appl. Polym. Sci. 2007, 104, 44
23. Ren, B.; Zhao, D.; Liu, S.; Liu, X.; Tong, Z. Macromolecules 2007, 40, 4501 and other references cited therein.
24. Overall average, values in entries 7-10 were calculated as 21 ± 2 for 1, 15 ± 1 for 2, 42 ± 2 for 3, and 22 ± 1 for 4 of the product distribution and as 11 ± 2 for 2* and 20 ± 2 for 3* of % ee.