Enantiodifferentiating photocyclodimerization of cyclohexa-1,3-diene sensitized by chiral arenecarboxylates

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 1, 2000, Pages 77-84

  Asaoka, Sadayuki ^a   Ooi, Motohiro ^a   Jiang, Peiyun ^a   Wada, Takehiko ^a   Inoue, Yoshihisa ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CHROMOPHORES; DIMERIZATION; DIMERS; OLEFINS; PHOTOCHEMICAL REACTIONS; PHOTOREACTIVITY; REACTION KINETICS; TEMPERATURE;

CHIRAL ARENECARBOXYLATES; CYCLOHEXADIENE; MICROENVIRONMENTAL POLARITY; PHOTOCYCLODIMERIZATION;

AROMATIC COMPOUNDS;

EID: 0033993089     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906826k     Document Type: Article

References (80)

1. (a) H. Rau, Chem. Rev., 1983, 83, 535
2. (b) Y. Inoue, Chem. Rev., 1992, 92, 471
3. (c) S. R. L. Everitt and Y. Inoue, in Organic Molecular Photochemistry, V. Ramamurthy and K. Schanze, Eds.; Marcel Dekker, New York, 1999; p. 71.
4. G. S. Hammond and R. S. Cole, J. Am. Chem. Soc., 1965, 87, 3256.
5. C. Ouannès, R. Beugelmans and G. Roussi, J. Am. Chem. Soc., 1973, 95, 8472.
6. G. Balavoine, S. Jugè and H. B. Kagan, Tetrahedron Lett., 1973, 4159.
7. (a) Y. Inoue, Y. Kunitomi, S. Takamuku and H. Sakurai, J. Chem. Soc., Chem. Commun., 1978, 1024
8. (b) Y. Inoue, S. Takamuku, Y. Kunitomi and H. Sakurai, J. Chem. Soc., Perkin Trans. 2, 1980, 1672
9. (c) S. Goto, S. Takamuku, H. Sakurai, Y. Inoue and T. Hakushi, ibid., 1980, 1678
10. (d) Y. Inoue, T. Yokoyama, N. Yamasaki and A. Tai, Nature, 1989, 341, 225
11. (e) Y. Inoue, T. Yokoyama, N. Yamasaki and A. Tai, J. Am. Chem. Soc., 1989, 111, 6480
12. (f) Y. Inoue, H. Shimoyama, N. Yamasaki and A. Tai, Chem. Lett., 1991, 593
13. (g) Y. Inoue, N. Yamasaki, T. Yokoyama and A. Tai, J. Org. Chem., 1992, 57, 1332
14. (h) Y. Inoue, N. Yamasaki, T. Yokoyama and A. Tai, J. Org. Chem., 1993, 58, 1011
15. (i) Y. Inoue, N. Yamasaki, H. Shimoyama and A. Tai, J. Org. Chem., 1993, 58, 1785
16. (j) Y. Inoue, H. Tsuneishi, T. Hakushi and A. Tai, J. Am. Chem. Soc., 1997, 119, 472
17. (k) Y. Inoue, E. Matsushima and T. Wada, J. Am. Chem. Soc., 1998, 120, 10687.
18. (a) O. Piva, F. Henin, J. Muzart and J.-P. Pete, Tetrahedron Lett., 1986, 27, 3001
19. (b) O. Piva, R. Mortezaei, F. Henin, J. Muzart and J.-P. Pete, J. Am. Chem. Soc., 1990, 112, 9263.
20. (a) H. Rau and M. Hormann, J. Photochem., 1981, 16, 231
21. (b) H. Rau and R. Ratz, Angew. Chem., 1983, 95, 552
22. H. Rau and R. Ratz, Angew. Chem., Int. Ed. Engl., 1983, 22, 550
23. (c) H. Rau and F. Totter, J. Photochem. Photobiol. A: Chem., 1992, 63, 337.
24. (a) M. Demuth, P. R. Raghavan, C. Carter, K. Nakano and K. Schaffner, Helv. Chim. Acta, 1980, 63, 2434
25. (b) M. Demuth, A. Palomer, H.-D. Sluma, A. K. Dey, C. Kruger and Y.-H. Tsay, Angew. Chem., 1986, 98, 1093
26. M. Demuth, A. Palomer, H.-D. Sluma, A. K. Dey, C. Kruger and Y.-H. Tsay, Angew. Chem., Int. Ed. Engl., 1986, 25, 117.
27. N. Hoshi, Y. Furukawa, H. Hagiwara, H. Uda and K. Sato, Chem. Lett., 1980, 47.
28. (a) K. Ohkubo, T. Hamada, T. Inaoka and H. Ishida, Inorg. Chem., 1989, 28, 2021
29. (b) K. Ohkubo, H. Ishida, T. Hamada and T. Inaoka, Chem. Lett., 1989, 1545.
30. T. Hikita, K. Tamaru, A. Yamagishi and T. Iwamoto, Inorg. Chem., 1989, 28, 2221.
31. K. Okada, H. Sakai, M. Oda, A. Yoshimura and T. Ohno, Tetrahedron Lett., 1989, 30, 1091.
32. Y. Inoue, T. Okano, N. Yamasaki and A. Tai, J. Photochem. Photobiol. A: Chem., 1992, 66, 61.
33. (a) N. J. Peacock and G. B. Schuster, J. Am. Chem. Soc., 1983, 105, 3632
34. (b) G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1984, 106, 6870
35. (c) G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1986, 108, 8021
36. (d) D. Hartsough and G. B. Schuster, J. Org. Chem., 1989, 54, 3
37. (e) N. Aubulut, D. Hartsough, J.-I. Kim and G. B. Schuster, J. Org. Chem., 1989, 54, 2549
38. (f) J.-I. Kim and G. B. Schuster, J. Am. Chem. Soc., 1990, 112, 9635.
39. (a) Y. Inoue, T. Okano, N. Yamasaki and A. Tai, J. Chem. Soc., Chem. Commun., 1993, 718
40. (b) S. Asaoka, T. Kitazawa, T. Wada and Y. Inoue, J. Am. Chem. Soc., 1999, 121, 8486.
41. F. Müller and J. Mattay, Chem. Rev., 1993, 93, 99.
42. T.-y. Wang, J.-d. Ni, J. Masnovi and N. C. Yang, Tetrahedron Lett., 1982, 23, 1231.
43. (a) W. K. Smothers and J. Saltiel, J. Am. Chem. Soc., 1983, 105, 2794
44. (b) J. Saltiel, R. Dabestani, D. F. Sears Jr., W. M. McGowan and E. F. Hilinski, J. Am. Chem. Soc., 1995, 117, 9129.
45. J. Mlcoch and E. Steckhan, Angew. Chem., Int. Ed. Engl., 1985, 24, 412
46. J. Mlcoch and E. Steckhan, Tetrahedron Lett., 1987, 28, 1081.
47. (a) J. Mattay, J. Gersdorf and J. Mertes, J. Chem. Soc., Chem. Commun., 1985, 1088
48. (b) J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825
49. (c) J. Mattay, G. Trampe and J. Runsink, Chem. Ber., 1988, 121, 1991
50. (d) J. Mattay, Nachr. Chem., Tech. Lab., 1988, 36, 376
51. (e) J. Mattay, M. Vondenhof and R. Denig, Chem. Ber., 1989, 122, 951
52. (f) W. S. Chung, N. J. Turro, J. Martes and J. Mattay, J. Org. Chem., 1989, 54, 4881
53. (g) J. Mattay, Synthesis, 1989, 233
54. (h) J. Mattay and M. Vondenhof, Chem. Ber., 1990, 123, 2457
55. J. Mattay and M. Vondenhof, Tetrahedron Lett., 1989, 30, 1091
56. (i) J. Mattay and M. Vondenhof, Top. Curr. Chem., 1991, 159, 219.
57. (a) D. Valentine, N. J. Turro and G. S. Hammond, J. Am. Chem. Soc., 1964, 86, 5202
58. (b) T. L. Penner, D. G. Whitten and G. S. Hammond, J. Am. Chem. Soc., 1970, 92, 2861.
59. G. O. Schenck, S. P. Mannsfeld, G. Schomburg and C. H. Krauch, Z. Naturforsch., Teil B, 1964, 19, 18.
60. (a) N. L. Bauld, D. J. Bellville, B. Harirchian, K. T. Lorenz, R. A. Pabon Jr., D. W. Reynolds, D. D. Wirth, H. S. Chiou and B. K. Marsh, Acc. Chem. Res., 1987, 20, 371
61. (b) D. J. Bellville, D. D. Wirth and N. L. Bauld, J. Am. Chem. Soc., 1981, 103, 718
62. (c) D. W. Raynolds, K. T. Lorenz, H. S. Chiou, D. J. Bellville, R. A. Padon and N. L. Bauld, J. Am. Chem. Soc., 1987, 109, 4960
63. (d) K. T. Lorenz and N. L. Bauld, J. Am. Chem. Soc., 1987, 109, 1157.
64. R. Schutte and G. R. Freeman, J. Am. Chem. Soc., 1969, 91, 3715.
65. K. Alder and G. Stein, Justus Liebigs Ann. Chem., 1932, 496, 197
66. K. Alder and G. Stein, Angew. Chem., 1933, 50, 514.
67. K. Mizuno, I. Nakanishi, N. Ichinose and Y. Otsuji, Chem. Lett., 1989, 1095.
68. (a) S. L. Mattes and S. Farid, Organic Photochemistry, A. Padwa, Ed.; Marcel Dekker, New York, NY, 1983; Vol. 6, Ch. 4
69. (b) M. Chanon and L. Eberson, Photoinduced Electron Transfer, M. A. Fox and M. Chanon, Eds.; Elsevier, Amsterdam, 1988, Part A, Ch. 1.11
70. F. D. Lewis, ibid., Part C, Ch. 4.1.
71. D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259.
72. The severe steric hindrance of 12a caused by four menthoxy-carbonyl groups would prevent the intimate electron-transfer interaction between the substrate and the sensitizer, resulting in the poor chemical yields.
73. C. R. Jones, B. J. Allman, A. Mooring and B. Spahic, J. Am. Chem. Soc., 1983, 105, 652.
74. S. L. Murov, Handbook of Photochemistry; Marcel Dekker, New York, 1973, p. 207.
75. If there is another path for the formation of exo-adduct 2b, the contribution of the direct formation path from the exciplex is reduced and the ee should be a higher value. Thus, the evaluated value is the lowest limit.
76. K. P. R. Kartha, Tetrahedron Lett., 1986, 27, 3415.
77. J. Kang, G. J. Lim, S. K. Yoon and M. Y. Kim, J. Org. Chem., 1995, 60, 564.
78. R. C. Hockett, R. E. Miller and A. Scattergood, J. Am. Chem. Soc., 1949, 71, 3072.
79. N. Yamasaki, Y. Inoue, T. Yokoyama, A. Tai, A. Ishida and S. Takamuku, J. Am. Chem. Soc., 1991, 113, 1933.
80. B. D. Baigrie, J. Brennan, J. I. G. Cadogan, J. Cook and J. T. Sharp, J. Chem. Soc., Perkin Trans. 1, 1975, 1060.