Folding-induced selective hydrogenation of helical 9,10-anthraquinone analogues

Organic Letters

Volumn 10, Issue 21, 2008, Pages 5035-5038

  Hu, Hai Yu ^a,b   Xiang, Jun Feng ^a   Cao, Jing ^a,b   Chen, Chuan Feng ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

9,10-ANTHRAQUINONE; ANTHRAQUINONE; ANTHRAQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTHRAQUINONES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDROGENATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY;

EID: 58149170365     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802241h     Document Type: Article

References (31)

1. (a) Hecht, S. M.; Huc, I. Foldamers: Structure, Properties and Applications; Wiley-VCH: Weinheim, Germany, 2007.
2. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
3. (c) Hill, D. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
4. Some recent reviews see: (a) Hue, I. Eur. J. Org. Chem. 2004, 1, 17-29.
5. (b) Gong, B.; Sanford, A. R.; Ferguson, J. S. Adv. Polym. Sci. 2007, 206, 1-29.
6. (c) Li, Z.-T.; Hou, J.-L.; Li, C.; Yi, H.-P. Chem. Asian J. 2006, 1, 766-778.
7. (d) Davis, J. M.; Tsou, L. K.; Hamilton, A. D. Chem. Soc. Rev. 2007, 36, 326-334.
8. (a) Breslow, R. Acc. Chem. Res. 1980, 13, 170-177.
9. (b) Smaldone, R. A.; Moore, J. S. Chem.-Eur. J. 2008, 14, 2650-2657.
10. (a) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668.
11. (b) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011.
12. (c) Vriezema, D. M.; Aragonès, M. C.; Elemans, J. A. A. W.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Chem. Rev. 2005, 105, 1445-1489.
13. (d) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
14. (a) Heemstra, J. M.; Moore, J. S. J. Am. Chem. Soc. 2004, 126, 1648-1649.
15. (b) Heemstra, J. M.; Moore, J. S. J. Org. Chem. 2004, 69, 9234-9237.
16. (c) Smaldone, R. A.; Moore, J. S. J. Am. Chem. Soc. 2007, 129, 5444-5450.
17. (d) Smaldone, R. A.; Moore, J. S. Chem. Commun. 2008, 1011-1013.
18. Dolain, C.; Zhan, C.; Léger, J. M.: Daniels, L.; Hue, I. J. Am. Chem. Soc. 2005, 127, 2400-2401.
19. Srinivas, K.; Kauffmann, B.; Dolain, C.; Léger, J. M.; Ghosez, L.; Hue, I. J. Am. Chem. Soc. 2008, 130, 13210-13211.
20. (a) Hu, Z.-Q.; Hu, H.-Y.; Chen, C.-F. J. Org. Chem. 2006, 71, 1131-1138.
21. (b) Hu, H.-Y.; Xiang, J.-F.; Yang, Y.; Chen, C.-F. Org. Lett. 2008, 10, 69-72.
22. (c) Hu, H.-Y.; Xiang, J.-F.; Yang. Y.; Chen, C.-F. Org. Lett. 2008, 10, 1275-1278.
23. See Supporting Information.
24. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
25. 2 = 0.3804 [I >2σ(I)].
26. Maurizot, V.; Dolain, C.; Leydet, Y.; Léger, J. M.; Guionneau, P.; Hue, I. J. Am. Chem. Soc. 2004, 126, 10049-10052.
27. To our surprise, no reductions of diacetamide anthraquinones were hitherto reported.
28. McCann, G. M.; McDonnell, C. M.; Magris, L.; O'Ferrall, R. A. M. J. Chem. Soc., Perkin Trans. 2 2002, 784-795.
29. 6-DMSO.
30. The reaction mechanism for formation of the dianthrone is not clear, which might be through a photoreaction under the influence of sunlight and air. For a similar reaction, see: Schönebrg, A.; Mustafa, A. J. Chem. Soc. 1945, 657-660. In addition, owing to the poor solubility of the dianthrone in common solvents, it has not been characterized by NMR and MS spectra.
31. 2 = 0.1455 [I > 2σ(I)].