Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by capped γ-cyclodextrins: Critical control of enantioselectivity by cap rigidity

Journal of Organic Chemistry

Volumn 73, Issue 15, 2008, Pages 5786-5794

  Yang, Cheng ^a   Mori, Tadashi ^a   Inoue, Yoshihisa ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CADMIUM COMPOUNDS; CIRCULAR DICHROISM SPECTROSCOPY; CYCLODEXTRINS; DICHROISM; ENANTIOSELECTIVITY; ENTHALPY; ENTROPY; GLUCOSE; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL PROPERTIES; PHOTORESISTS; RIGIDITY; SILANES; THERMODYNAMICS;

ABSOLUTE CONFIGURATION (AC); AMERICAN CHEMICAL SOCIETY (ACS); ANTHRACENECARBOXYLIC ACID; AROMATIC GROUPS; BIPHENYL (BP); BIPHENYL GROUP; CIRCULAR DICHROISM (DC); CYCLODEXTRIN (CYDS); CYCLODEXTRINS (CDS); D-GLUCOSE; DIFFERENTIAL ENTHALPY; DIFFERENTIAL ENTROPY; ENANTIO-DIFFERENTIATION; ENANTIOMERIC EXCESS (EE); ENTROPY CHANGES; ENTROPY COMPENSATION; HIGHLY SENSITIVE; HOST GUEST COMPLEXES; NMR SPECTROS COPY; PHOTOCYCLODIMERIZATION; TEMPERATURE VARIATIONS;

DATA STORAGE EQUIPMENT;

ANTHRACENE DERIVATIVE; AROMATIC COMPOUND; BIPHENYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIMER; GAMMA CYCLODEXTRIN DERIVATIVE; GLUCOSE;

ARTICLE; CIRCULAR DICHROISM; COMPLEX FORMATION; CYCLIZATION; DIMERIZATION; ENANTIOMER; ENANTIOSELECTIVITY; ENTHALPY; ENTROPY; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE SENSITIVITY; ULTRAVIOLET SPECTROSCOPY;

EID: 48249119565     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800533y     Document Type: Article

References (68)

1. (a) Inoue, Y.; Ramamurthy, V. Chiral Photochemistry; Marcel Dekker: New York, 2004.
2. (b) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
3. (c) Griesbeck, A. G.; Meierhenrich, U. J. Angew Chem., Int. Ed. 2002, 41, 3147.
4. (d) Turro, N. J Pure Appl. Chem. 1995, 67, 199.
5. (e) McClenaghan, N. D.; Absalon, C.; Bassani, D. M. J. Am. Chem. Soc. 2003, 125, 13004.
6. (a) Inoue, Y. Chem. Rev. 1992, 92, 741.
7. (b) Rau, H. Chem. Rev. 1983, 83, 535.
8. (a) YangC.; Inoue, Y. In Cyclodextrin Materials Photochemistry, Photophysics and Photobiology; Douhal, A., Ed.;Elsevier: New York, 2006; pp241-265.
9. (b) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
10. (c) Takahashi, K Chem. Rev. 1998, 98, 2013.
11. (d) Rao, V. P.; Turro, N. J. Tetrahedron Lett. 1989, 30, 4641.
12. (e) Shailaja, J.; Karthikeyan, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9335.
13. (f) Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529.
14. (g) Inoue, Y.; Dong, F.; Yamamoto, K.; Tong, L.-H.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1995, 117, 11033.
15. (h) Fleck, M.; Yang, C.; Wada, T.; Inoue, Y.; Bach, T. Chem. Commun. 2007, 822.
16. (a) Sugahara, N.; Kawano, M.; Wada, T.; Inoue, Y. Nucleic Acids Symp. Ser. 2000, 115.
17. (b) Wada, T.; Nishijima, M.; Fujisawa, T.; Sugahara, N.; Mori, T.; Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 7492.
18. (c) Nishijima, M.; Pace, T. C. S.; Nakamura, A.; Mori, T.; Wada, T.; Bohne, C.; Inoue, Y. J. Org. Chem. 2007, 72, 2707.
19. (d) Nishijima, M.; Wada, T.; Mori, T.; Pace, T. C. S.; Bohne, C.; Inoue, Y. J. Am. Chem. Soc. 2007, 129, 3478.
20. (e) Lhiaubet-Vallet, V.; Encinas, S.; Miranda, M. A. J. Am. Chem. Soc. 2005, 127, 12774.
21. (a) Joy, A.; Ramamurthy, V. Chemistry 2000, 6, 1287.
22. (b) Sivaguru, J.; Natarajan, A.; Kaanumalle, L. S.; Shailaja, J.; Uppili, S.; Joy, A.; Ramamurthy, V. Acc. Chem. Res. 2003, 36, 509.
23. (c) Sivaguru, J.; Poon, T.; Franz, R.; Jockusch, S.; Adam, W.; Turro, N. J. J. Am. Chem. Soc. 2004, 126, 10816.
24. (a) Aechtner, T.; Dressel, M.; Bach, T. Angew. Chem., Int. Ed. 2004, 43, 5849.
25. (b) Bauer, A.; Weskamper, F.; Grimme, S.; Bach, T. Nature 2005, 1139.
26. (c) Inoue, Y. Nature 2005, 1099.
27. (d) Mizoguchi, J.-i.; Kawanami, Y.; Wada, T.; Kodama, K.; Anzai, K.; Yanagi, T.; Inoue, Y. Org. Lett. 2006, 8 (26), 6051.
28. (a) Rekharsky, M. V.; Inoue, Y Chem. Rev. 1998, 98, 1875.
29. (b) Nelson, A.; Belitsky, J. M.; Vidal, S.; Joiner, C. S.; Baum, L. G.; Stoddart, J. F. J. Am. Chem. Soc. 2004, 126, 11914.
30. (d) Liu, Y.; Yu, H. M.; Chen, Y.; Zhao, Y. L. Chem. Eur. J. 2006, 3858.
31. (e) Tomatsu, I.; Hashidzume, A.; Harada, A. J. Am. Chem. Soc. 2006, 128, 2226.
32. (f) Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, N.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y; Kaifer, A. E.; Kim, K. J. Am. Chem. Soc. 2005, 127, 12984.
33. (a) V. P., Rao; N. J., Turro Tetrahedron Lett. 1989, 30, 4641.
34. (b) Inoue, Y.; Wada, T.; Sugahara, N.; Yamamoto, K.; Kimura, K.; Tong, L.-H.; Gao, X.-M.; Hou, Z.-J.; Liul, Y. J. Org. Chem. 2000, 65, 8041.
35. (c) Inoue, Y.; Dong, S. F.; Yamamoto, K.; Tong, L.-H.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1995, 113, 2793.
36. (d) Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2005, 4199.
37. (e) Koodanjeri, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9229.
38. (f) Shailaja, J.; Karthikeyan, S.; Ramamurthy, V Tetrahedron Lett. 2002, 43, 9335.
39. (g) Koodanjeri, S.; Joy, A.; Ramamurthy, V. Tetrahedron 2000, 56, 7003.
40. (h) Vizvardi, K.; Desmet, K.; Luyten, I.; Sandra, P.; Hoornaert, G.; Van der Eycken, E. Org. Lett. 2001, 3, 1173.
41. (i) Mori, T.; Weiss, R. G.; Inoue, Y. J. Am. Chem. Soc. 2004, 126, 8961.
42. (j) Yang, C.; Mori, T.; Wada, T.; Inoue, Y. New J. Chem. 2007, 31, 697.
43. (a) Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 966.
44. (b) 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.
45. (c) Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2005, 127, 5338.
46. (d) Yang, C.; Nakamura, A.; Fukuhara, G.; Origane, Y.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 3126.
47. (e) Yang, C.; Nakamura, A.; Wada, T.; Inoue, Y. Org. Lett. 2006, 8, 3005.
48. (a) Engeldinger, E.; Armspach, D.; Matt, D. Chem. Rev. 2003, 103, 4147.
49. (b) Rudzinski, C. M.; Young, A. M.; Nocera, D. G. J. Am. Chem. Soc. 2002, 124, 1723.
50. (c) Tabushi, I.; Shimokawa, K.; Shimizu, N.; Shirakata, H.; Fujita, K. J. Am. Chem. Soc. 1976, 98, 7855.
51. (d) Fujita, K.; Shinoda, A.; Imoto, T. J. Am. Chem. Soc. 1980, 102, 1161.
52. (e) Breslow, R.; Canary, J. W.; Varney, M.; Waddell, S. T.; Yang, D. J. Am. Chem. Soc. 1990, 112, 5212.
53. See Supporting Information.
54. Kodaka, M. J. Am. Chem. Soc. 1993, 115, 3702.
55. (a) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
56. (b) Hoffmann, R.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 10702.
57. (a) Zhang, X.; Gramlich, G.; Wang. X.; Nau, W. M. J. Am. Chem. Soc. 2002, 124, 254.
58. (b) Dyck, A. S. M.; Kisiel, U.; Bohne, C. J. Phys. Chem. B 2003, 107, 11652.
59. Tamaki, T.; Kokubu, T.; Ichimura, K. Tetrahedron 1987, 43, 1485.
60. (a) Corbett, P. T.; Tong, L. H.; Sanders, J. K. M.; Otto, S. J. Am. Chem. Soc. 2005, 127, 8902.
61. (b) Kasai, K.; Aoyagi, M.; Fujita, M. J. Am. Chem. Soc. 2000, 122, 2140,
62. Bender, M. L.; Van Etten, R. L.; Clowes, G. A.; Sebastian. J. F. J. Am. Chem. Soc. 1966, 88, 2318,
63. (a) Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions; Wiley: New York, 1963; reprint version from Dover, New York, 1989.
64. (b) Grunwald, E.; Steel, C. J. Am. Chem. Soc. 1995, 117, 5687.
65. (c) Exner, O. Correlation Analysis of Chemical Data; Plenum: New York, 1988.
66. Very recently, the only exceptions from the compensatory enthalpy-entropy relationship have been reported for a cucurbit[7]uril-ferrocene system: Rekharsky, M. V.; Mori, T.; Yang, C.; Ko, Y. H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A. E.; Liu, S.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M. K.; Kim, K.; Inoue, Y. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 20737.
67. For earlier examples and analyses of the compensatory enthalpy-entropy relationship in various supramolecuar systems, see: Inoue, Y.; Wada, T. Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 4, pp 55-96.
68. Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943.