Switching of product's chirality in diastereodifferentiating [2+2] photocycloaddition of (E)- versus (Z)-stilbene to chiral fumarate upon direct and charge-transfer-band excitation

Organic Letters

Volumn 8, Issue 9, 2006, Pages 1909-1912

  Saito, Hideaki ^a   Mori, Tadashi ^a,c   Wada, Takehiko ^a   Inoue, Yoshihisa ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646437918     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060468s     Document Type: Article

References (17)

1. Inoue, Y.; Ramamurthy, V. Chiral Photochemistry; Marcel Dekker: New York, 2004.
2. Inoue, Y. Chem. Rev. 1992, 92, 741.
3. Rau, H. Chem. Rev. 1983, 83, 535.
4. Inoue, Y. Nature 2005, 436, 1099-1100.
5. Inoue, Y.; Wada, T.; Asaoka, S.; Sato, H.; Pete, J.-P. Chem. Commun. 2000, 251.
6. Bach, T.; Bergmann, H. J. Am. Chem. Soc. 2000, 122, 11525.
7. Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139.
8. Wada, T.; Nishijima, M.; Fujisawa, T.; Sugahara, N.; Mori, T.; Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 7492.
9. Suzuki, T.; Ichioka, K.; Higuchi, H.; Kawai, H.; Fujiwara, K.; Ohkita, M.; Tsuji, T.; Takahashi, Y. J. Org. Chem. 2005, 70, 5592.
10. Saito, H.; Mori, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 2004, 126, 1900.
11. Saito, H.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2004, 1652.
12. Foster, R. Organic Charge-Transfer Complexes; Adademic Press: New York, 1969.
13. McGlynn, S. P. Chem. Rev. 1958, 58, 1113.
14. Mulliken, R. S.; Person, W. B. Annu. Rev. Phys. Chem. 1962, 13, 107.
15. Saltiel, J.; Marinari, A.; Chang, D. W. L.; Mitchener, J. C.; Megarity, E. D. J. Am. Chem. Soc. 1979, 101, 2982.
16. Waldeck, D. H. Chem. Rev. 1991, 91, 415.
17. Green, B. S.; Rejto, M.; Johnson, D. E.; Hoyle, C. E.; Simpson, J. T.; Correa, P. E.; Ho, T. I.; McCoy, F.; Lewis, F. D. J. Am. Chem. Soc. 1979, 101, 3325.