Enantiodifferentiating anti-Markovnikov photoaddition of alcohols to 1,1-diphenylalkenes sensitized by chiral naphthalenecarboxylates

Journal of the American Chemical Society

Volumn 121, Issue 37, 1999, Pages 8486-8498

  Asaoka, Sadayuki ^a   Kitazawa, Toshiya ^a   Wada, Takehiko ^a   Inoue, Yoshihisa ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHOIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; CONCENTRATION (PARAMETERS); ENANTIOMER; ENTROPY; FLUORESCENCE; IRRADIATION; PHOTOCHEMISTRY; PHOTOSENSITIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 0033595490     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9909374     Document Type: Article

References (55)

1. For reviews, see: (a) Rau, H. Chem. Rev. 1983, 83, 535. (b) Inoue, Y. Chem. Rev. 1992, 92, 471. Everitt, S. R. L.; Inoue, Y. In Molecular and Supramolecular Photochemisty; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1999; Vol. 3, p 71.
2. For reviews, see: (a) Rau, H. Chem. Rev. 1983, 83, 535. (b) Inoue, Y. Chem. Rev. 1992, 92, 471. Everitt, S. R. L.; Inoue, Y. In Molecular and Supramolecular Photochemisty; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1999; Vol. 3, p 71.
3. For reviews, see: (a) Rau, H. Chem. Rev. 1983, 83, 535. (b) Inoue, Y. Chem. Rev. 1992, 92, 471. Everitt, S. R. L.; Inoue, Y. In Molecular and Supramolecular Photochemisty; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1999; Vol. 3, p 71.
4. Hammond, G. S.; Cole, R. S. J. Am. Chem. Soc. 1965, 87, 3256.
5. Ouannès, C.; Beugelmans, R.; Roussi, G. J. Am. Chem. Soc. 1973, 95, 8472.
6. Balavoine, G.; Jugè, S.; Kagan, H. B. Tetrahedron Lett. 1973, 4159.
7. (a) Inoue, Y.; Kunitomi, Y.; Takamuku, S.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 1024.
8. (b) Inoue, Y.; Takamuku, S.; Kunitomi, Y.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1980, 1672.
9. (c) Goto, S.; Takamuku, S.; Sakurai, H.; Inoue, Y.; Hakushi, T. ibid. 1980, 1678.
10. (d) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. Nature 1989, 341, 225.
11. (e) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
12. (f) Inoue, Y.; Shimoyama, H.; Yamasaki, N.; Tai, A. Chem. Lett. 1991, 593.
13. (g) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332.
14. (h) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011.
15. (i) Inoue, Y.; Yamasaki, N.; Shimoyama, H.; Tai, A. J. Org. Chem. 1993, 58, 1785.
16. (j) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472.
17. (k) Inoue, Y.; Matsushima, E.; Wada, T. J. Am. Chem. Soc. 1998, 120, 10687.
18. (a) Piva, O.; Henin, F.; Muzart, J.; Pete, J.-P. Tetrahedron Lett. 1986, 27, 3001.
19. (b) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.; Pete, J.-P. J. Am. Chem. Soc. 1990, 112, 9263.
20. (a) Rau, H.; Hormann, M. J. Photochem. 1981, 16, 231.
21. (b) Rau, H.; Ratz, R. Angew. Chem. 1983, 95, 552; Angew. Chem., Int. Ed. Engl. 1983, 22, 550.
22. (b) Rau, H.; Ratz, R. Angew. Chem. 1983, 95, 552; Angew. Chem., Int. Ed. Engl. 1983, 22, 550.
23. Rau, H.; Totter, F. J. Photochem. Photobiol., A 1992, 63, 337.
24. (a) Demuth, M.; Raghavan, P. R.; Carter, C.; Nakano, K.; Schaffner, K. Helv. Chim. Acta 1980, 63, 2434.
25. (b) Demuth, M.; Palomer, A.; Sluma, H.-D.; Dey, A. K.; Kruger, C.; Tsay, Y.-H. Angew. Chem. 1986, 98, 1093; Angew. Chem., Int. Ed. Engl. 1986, 25, 117.
26. (b) Demuth, M.; Palomer, A.; Sluma, H.-D.; Dey, A. K.; Kruger, C.; Tsay, Y.-H. Angew. Chem. 1986, 98, 1093; Angew. Chem., Int. Ed. Engl. 1986, 25, 117.
27. Hoshi, N.; Furukawa, Y.; Hagiwara, H.; Uda, H.; Sato, K. Chem. Lett. 1980, 47.
28. (a) Vondenhof, M.; Mattay, J. Chem. Ber. 1990, 123, 2457.
29. (b) Vondenhof, M.; Mattay, J. Tetrahedron Lett. 1990, 31, 985.
30. (a) Ohkubo, K.; Hamada, T.; Inaoka, T.; Ishida, H. Inorg. Chem. 1989, 28, 2021.
31. (b) Ohkubo, K.; Ishida, H.; Hamada, T.; Inaoka, T. Chem. Lett. 1989, 1545.
32. Hikita, T.; Tamara, K.; Yamagishi, A.; Iwamoto, T. Inorg. Chem. 1989, 28, 2221.
33. Okada, K.; Sakai, H.; Oda, M.; Yoshimura, A.; Ohno, T. Tetrahedron Lett. 1989, 30, 1091.
34. Inoue, Y.; Okano, T.; Yamasaki, N.; Tai, A. J. Photochem. Photobiol., A 1992, 66, 61.
35. Kim, J.-I.; Schuster, G. B. J. Am. Chem. Soc. 1990, 112, 9635.
36. Inoue, Y.; Okano, T.; Yamasaki, N.; Tai, A. J. Chem. Soc., Chem. Commun. 1993, 718.
37. Mizuno, K.; Nakanishi. I.; Ichinose, N.; Otsuji, Y. Chem. Lett. 1989, 1095.
38. For reviews, see: (a) Mattes, S. L.; Farid, S. Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1983; Vol. 6, Chapter 4. (b) Chanon, M.; Eberson, L. Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, The Netherlands, 1988; Part A, Chapter 1.11; Lewis, F. D. ibid., Part C, Chapter 4.1.
39. For reviews, see: (a) Mattes, S. L.; Farid, S. Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1983; Vol. 6, Chapter 4. (b) Chanon, M.; Eberson, L. Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, The Netherlands, 1988; Part A, Chapter 1.11; Lewis, F. D. ibid., Part C, Chapter 4.1.
40. For reviews, see: (a) Mattes, S. L.; Farid, S. Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1983; Vol. 6, Chapter 4. (b) Chanon, M.; Eberson, L. Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, The Netherlands, 1988; Part A, Chapter 1.11; Lewis, F. D. ibid., Part C, Chapter 4.1.
41. (a) Kubo, Y.; Inoue, T.; Sakai, H. J. Am. Chem. Soc. 1992, 114, 7660.
42. (b) Kubo, Y.; Adachi, T.; Miyahara, N.; Nakajima, S.; Inamura, I. Tetrahedron Lett. 1998, 39, 9477.
43. (c) Kubo, Y.; Yoshioka, M.; Nakajima, S.; Inamura, I. Tetrahedron Lett. 1999, 40, 2335.
44. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
45. The severe steric hindrance of 10a caused by the two menthoxycarbonyl groups at the adjacent peri positions would prevent the intimate electron-transfer interaction between the substrate and the sensitizer, resulting in poor chemical yield.
46. T value; for reviews, see: (a) Reichardt, C. Solvent Effects in Organic Chemistry; Verlag Chemie: Weinheim, Germany, 1979. (b) Reichardt, C. Chem. Rev. 1994, 94, 2319.
47. T value; for reviews, see: (a) Reichardt, C. Solvent Effects in Organic Chemistry; Verlag Chemie: Weinheim, Germany, 1979. (b) Reichardt, C. Chem. Rev. 1994, 94, 2319.
48. Murov, S. L.; Handbook of Photochemistry; Marcel Dekker: New York, 1973; p 207.
49. Wagner, P. J., Tetrahedron Lett. 1968, 5385.
50. Haller, R.; Schneider, H. J. Arch. Pharm. (Weinheim, Ger.) 1973, 306, 846.
51. Serijan, K. T.; Wise, P. H. J. Am. Chem. Soc. 1951, 73, 4766.
52. (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908.
53. (b) Ensley, H. E.; Parnell, C. A.; Corey, E. J. J. Org. Chem. 1978, 43, 1610.
54. Glen, W. L.; Gordon, S. M.; Barber, R. J.; Grant, G. A. Am. Horme. Product. Corp. 1955, Aug, 9.
55. Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y. J. Org. Chem. 1995, 60, 564.