Diastereodifferentiating Z-E photoisomerization of 3- benzoyloxycyclooctene: Diastereoselectivity switching controlled by substrate concentration through competitive intra- vs intermolecular photosensitization processes [4]

Journal of the American Chemical Society

Volumn 121, Issue 42, 1999, Pages 9877-9878

  Inoue, Toru ^a   Matsuyama, Keisuke ^a   Inoue, Yoshihisa ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

CHIRALITY; DIASTEREOISOMER; GAS CHROMATOGRAPHY; ISOMERISM; LETTER; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOSENSITIZATION;

EID: 0033610497     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9918371     Document Type: Letter

References (17)

1. Rau, H. Chem. Rev. 1983, 83, 535.
2. Inoue, Y. Chem. Rev. 1992, 92, 741. Everitt, S. R. L.; Inoue, Y. In Organic Molecular Photochemistry; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1999; p 71.
3. Inoue, Y. Chem. Rev. 1992, 92, 741. Everitt, S. R. L.; Inoue, Y. In Organic Molecular Photochemistry; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1999; p 71.
4. Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
5. Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332.
6. Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai A. J. Org. Chem. 1993, 58, 1011.
7. Inoue, Y.; Matsushima, E.; Wada T. J. Am. Chem. Soc. 1998, 120, 10687.
8. Strickland, A. D.; Caldwell, R. A. J. Phys. Chem. 1993, 97, 13394.
9. Tsuneishi, H.; Inoue, Y.; Hakushi, T.; Tai, A. J. Chem. Soc., Perkin Trans. 2 1993, 457.
10. Tsuneishi, H.; Hakushi, T.; Tai, A.; Inoue, Y. J. Chem. Soc., Perkin Trans. 2 1995, 2057.
11. The diastereodifferentiating photoisomerization of cyclooctene derivatives has been achieved by the introduction of a chiral auxiliary at the olefinic position: Sugimura, T.; Shimizu, H.; Umemoto, S.; Tsuneishi, H.; Hakushi, T.; Inoue, Y.; Tai, A. Chem. Lett. 1998, 323.
12. Denmark, S. E.; Su, X.; Nishigaichi, Y. J. Am. Chem. Soc. 1998, 120, 12990.
13. Alvarez-Ibarra, C.; Csáky, A. G.; Murcia, M. C. J. Org. Chem. 1998, 63, 8736.
14. Kobayashi, S.; Kawasuji, T. Tetrahedron Lett. 1994, 20, 3329.
15. The asterisk represents t1he relative configuration of the two stereogenic centers.
16. The initial de value was estimated by extrapolating the de values observed at shorter irradiation periods to time zero.
17. It is also noted that the de of the product deviated slightly from the initial value in each run, approaching the photostationary state upon prolonged irradiation. Judging from the similarity in the time profiles of the de and E/Z ratios, this deviation may be attributable to the diastereodifferentiating E-Z photoisomerization, in which the preferential diastereomer of 1E has a tendency to undergo the reverse process slightly more effectively.