Efficient diastereodifferentiating E-Z photoisomerization of cyclooctene tethered to intramolecular sensitizer through optically active pentane-2,4-diyl unit

Chemistry Letters

Volumn , Issue 4, 1998, Pages 323-324

  Sugimura, Takashi ^a   Shimizu, Hitoshi ^a   Umemoto, Shin'ichi ^a   Tsuneishi, Hiroshi ^a   Hakushi, Tadao ^a   Inoue, Yoshihisa ^b   Tai, Akira ^a  

^a UNIVERSITY OF HYOGO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032383298     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.323     Document Type: Article

References (10)

1. H. Rau, Chem. Rev., 83, 535 (1983); Y. Inoue, Chem. Rev., 92, 441 (1992). J.-P. Pete, Adv. Photochem., 21, 135 (1996).
2. H. Rau, Chem. Rev., 83, 535 (1983); Y. Inoue, Chem. Rev., 92, 441 (1992). J.-P. Pete, Adv. Photochem., 21, 135 (1996).
3. H. Rau, Chem. Rev., 83, 535 (1983); Y. Inoue, Chem. Rev., 92, 441 (1992). J.-P. Pete, Adv. Photochem., 21, 135 (1996).
4. a) Y. Inoue, T. Yokoyama, N. Yamasaki, and A. Tai, J. Am. Chem. Soc., 111, 6480 (1989);
5. b) Y. Inoue, N. Yamasaki, T. Yokoyama, and A. Tai, J. Org. Chem., 57, 1332 (1992); Y. Inoue, N. Yamasaki, T. Yokoyama, and A. Tai, J. Org. Chem., 58, 1011 (1993).
6. b) Y. Inoue, N. Yamasaki, T. Yokoyama, and A. Tai, J. Org. Chem., 57, 1332 (1992); Y. Inoue, N. Yamasaki, T. Yokoyama, and A. Tai, J. Org. Chem., 58, 1011 (1993).
7. Y. Inoue, F. Dong, K. Yamamoto, L.-H. Tong, H. Tsuneishi, T. Hakushi, and A. Tai, J. Am. Chem. Soc., 117, 11033 (1995).
8. The photolysis at 85 °C was carried out in octane.
9. Stereochemistries of the major diastereomers of (Z)-4, (Z)-5 and (Z)-6 were unknown, but were determined to be same by hydrolysis and re-esterification experiments.
10. Unpublished result: the photosensitization of 1 with (R,R)-2,4-pentanediol dibenzoate gave 0.8% ee in pentane at 25 °C.