Absolute asymmetric photocyclization of a photochromic diarylethene derivative in single crystals

Angewandte Chemie - International Edition

Volumn 42, Issue 14, 2003, Pages 1636-1639

  Yamamoto, Satoshi ^a   Matsuda, Kenji ^a   Irie, Masahiro ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chirality; Enantioselectivity; Photochemistry; Photochromism

Indexed keywords

DERIVATIVES; ISOMERS; SINGLE CRYSTALS; ULTRAVIOLET RADIATION;

PHOTOCYCLIZATION;

CRYSTAL LATTICES;

ETHYLENE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; ENANTIOSELECTIVITY; PHOTOCHEMISTRY; RING OPENING; STRUCTURE ANALYSIS; ULTRAVIOLET RADIATION;

EID: 0037432917     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250417     Document Type: Article

References (49)

1. a) Photochemistry in Organized and Constrained Media (Ed.: V. Ramamurthy), VCH, Weinheim, 1991;
2. b) V. Ramamurthy, K. Venkatesan, Chem. Rev. 1987, 87, 433-481;
3. c) F. Toda, Acc. Chem. Res. 1995, 28, 480-486;
4. d) J. N. Gamlin, R. Jones, M. Leibovitch, B. Patrick, J. R. Scheffer, J. Trotter, Acc. Chem. Res. 1996, 29, 203-209;
5. e) K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074.
6. a) J. Hu, L.-S. Li, W. Yang, L. Manna, L.-W. Wang, A. P. Alivisatos, Science 2001, 292, 2060-2063;
7. b) L. Pavesi, L. Dal Negro, C. Mazzoleni, G. Franzò, F. Priolo, Nature 2000, 408, 440-444;
8. c) Z. Ding, B. M. Quinn, S. K. Haram, L. E. Pell, B. A. Korgel, A. J. Bard, Science 2002, 296, 1293-1297.
9. a) V. R. Pedireddi, A. R. P. Sarma, G. R. Desiraju, J. Chem. Soc. Perkin Trans. 2 1992, 311-320;
10. b) Y. Ito, B. Borecka, G. Olovsson, J. Trotter, J. R. Scheffer, Tetrahedron Lett. 1995, 36, 6087-6090;
11. c) S. H. Shin, A. E. Keating, M. A. Garcia-Garibay, J. Am. Chem. Soc. 1996, 118, 7626-7627;
12. d) D. G. Amirsakis, M. A. Garcia-Garibay, S. J. Rowan, J. F. Stoddart, A. J. P. White, D.J. Williams, Angew. Chem. 2001, 113, 4386-4391; Angew. Chem. Int. Ed. 2001, 40, 4256-4261.
13. d) D. G. Amirsakis, M. A. Garcia-Garibay, S. J. Rowan, J. F. Stoddart, A. J. P. White, D.J. Williams, Angew. Chem. 2001, 113, 4386-4391; Angew. Chem. Int. Ed. 2001, 40, 4256-4261.
14. a) H. Aoyama, T. Hasegawa, Y. Omote, J. Am. Chem. Soc. 1979, 101, 5343-5347;
15. b) F. Toda, K. Tanaka, Tetrahedron Lett. 1986, 29, 4299-4302;
16. c) F. Toda, K. Tanaka, O. Kakinoki, T. Kawakami,J. Org. Soc. 1993, 58, 3783-3784;
17. d) K. Tanaka, F. Toda, E. Mochizuki, N. Yasui, Y. Kai, I. Miyahara, K. Hirotsu, Angew. Chem. 1999, 111, 3733-3736; Angew. Chem. Int. Ed. 1999, 38, 3523-3525;
18. d) K. Tanaka, F. Toda, E. Mochizuki, N. Yasui, Y. Kai, I. Miyahara, K. Hirotsu, Angew. Chem. 1999, 111, 3733-3736; Angew. Chem. Int. Ed. 1999, 38, 3523-3525;
19. e) H. Hosomi, S. Ohba, K. Tanaka, F. Toda, J. Am. Chem. Soc. 2000, 122, 1818-1819.
20. a) A. G. Schultz, A. G. Taveras, R. E. Taylor, F. S. Tham, R. K. Kulling, J. Am. Chem. Soc. 1992, 114, 8725-8727;
21. b) M. Sakamoto, M. Takahashi, N. Hokari, T. Fujita, S. Watanabe, J. Org. Chem. 1994, 59, 3131-3134;
22. c) Y. Ito, G. Kano, N. Nakamura, J. Org. Chem. 1998, 63, 5643-5647.
23. K. Penzien, G. M. J. Schmidt, Angew. Chem. 1969, 81, 628-629; Angew. Chem. Int. Ed. Engl. 1969, 8, 608-609.
24. K. Penzien, G. M. J. Schmidt, Angew. Chem. 1969, 81, 628-629; Angew. Chem. Int. Ed. Engl. 1969, 8, 608-609.
25. S. V. Evans, M. Garcia-Garibay, N. Omkaram, J. R. Scheffer, J. Trotter, F. Wireko, J. Am. Chem. Soc. 1986, 108, 5648-5650.
26. L. Addadi, J. van Mil, M. Lahav, J. Am. Chem. Soc. 1982, 104, 3422-3429.
27. C. M. Chung, M. Hasegawa, J. Am. Chem. Soc. 1991, 113, 7311-7316.
28. a) M. Irie, Chem. Rev. 2000, 100, 1685-1716;
29. b) K. Matsuda, K. Takayama, M. Irie, Chem. Commun. 2001, 363-364;
30. c) K. Shibata, K. Muto, S. Kobatake, M. Irie, J. Phys. Chem. A 2002, 106, 209-214;
31. d) K. Higashiguchi, K. Matsuda, M. Matsuo, T. Yamada, M. Irie, J. Photochem. Photobiol. A 2002, 152, 141-146;
32. e) M. Morimoto, S. Kobatake, M. Irie. Adv. Mater. 2002, 14, 1027-1029;
33. f) T. Yamada, S. Kobatake, M. Irie, Bull. Chem. Soc. Jpn. 2002, 75, 167-173.
34. T. Yamaguchi, K. Uchida, M. Irie, J. Am. Chem. Soc. 1997, 119, 6066-6071.
35. E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. 2001, 113, 1802-1805; Angew. Chem. Int. Ed. 2001, 40, 1752-1755.
36. E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. 2001, 113, 1802-1805; Angew. Chem. Int. Ed. 2001, 40, 1752-1755.
37. a) T. Kodani, K. Matsuda, T. Yamada, M. Irie, Chem. Lett. 1999, 1003-1004;
38. b) T. Kodani, K. Matsuda, T. Yamada, S. Kobatake, M. Irie, J. Am. Chem. Soc. 2000, 122, 9631-9637;
39. c) K. Matsuda, S. Yamamoto, M. Irie, Tetrahedron Lett. 2001, 42, 7291-7293.
40. 2: C 60.41, H 3.15; found: C 60.28, H 3.16.
41. 2 = 0.1290 (for all data), Flack parameter χ = -0.02(12). CCDC-194695 ((P)-1a), CCDC-194696 ((P)-1a'), and CCDC-194694 ((M)-1a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
42. -1).
43. a) J. Harada, H. Uekusa, Y. Ohashi, J. Am. Chem. Soc. 1999, 121, 5809-5810;
44. b) M. Kawano, T. Sano, J. Abe, Y. Ohashi, J. Am. Chem. Soc. 1999, 121, 8106-8107;
45. c) M. Kawano, T. Sano, J. Abe, Y. Ohashi, Chem. Lett. 2000, 1372-1373;
46. d) S. Kobatake, K. Shibata, K. Uchida, M. Irie, J. Am. Chem. Soc. 2000, 122, 12135-12141;
47. e) T. Yamada, K. Muto, S. Kobatake, M. Irie, J. Org. Chem. 2001, 66, 6164-6168;
48. f) T. Yamada, S. Kobatake, K. Muto, M. Irie, J. Am. Chem. Soc. 2000, 122, 1589-1592;
49. g) T. Yamada, S. Kobatake, M. Irie, Bull. Chem. Soc. Jpn. 2000, 73, 2179-2184.