Chemistry of unique chiral olefins. 3. Synthesis and absolute stereochemistry of trans- and cis-1,1',2,2',3,3',4,4'-octahydro-3,3'-dimethyl-4,4'- biphenanthrylidenes

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7256-7264

  Harada, Nobuyuki ^a   Koumura, Nagatoshi ^a   Feringa, Ben L ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PHENANTHRENE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PHOTOCHEMISTRY; STEREOCHEMISTRY; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 0030852810     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970669e     Document Type: Article

References (16)

1. See papers of this series: (a) (part 1) Harada, N.; Saito, A.; Koumura, N.; Uda, H.; de Lange, B.; Jager, W. F.; Wynberg, H.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 7241. (b) (part 2) Harada, N.; Saito, A.; Koumura, N.; Roe, D. C.; Jager, W. F.; Zijlstra, R. W. J.; de Lange, B.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 7249.
2. See papers of this series: (a) (part 1) Harada, N.; Saito, A.; Koumura, N.; Uda, H.; de Lange, B.; Jager, W. F.; Wynberg, H.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 7241. (b) (part 2) Harada, N.; Saito, A.; Koumura, N.; Roe, D. C.; Jager, W. F.; Zijlstra, R. W. J.; de Lange, B.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 7249.
3. (a) Harada, N.; Soutome, T.; Murai, S.; Uda, H. Tetrahedron: Asymmetry 1993, 4, 1755.
4. (b) Harada, N.; Soutome, T.; Nehira, T.; Uda, H.; Oi, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc. 1993, 115, 7547.
5. (c) Hagiwara, H.; Okamoto, T.; Harada, N.; Uda, H. Tetrahedron 1995, 51, 9891 and references cited therein.
6. See also: Toyota, S.; Miyasaka, T.; Matsumoto, Y.; Matsuo, T.; Oki, M. Bull. Chem. Soc. Jpn. 1994, 67, 1680.
7. (a) Harada, N.; Nehira, T.; Soutome, T.; Hiyoshi, N.; Kido, F. Enantiomer 1996, 1, 35.
8. (b) Harada, N.; Koumura, N.; Robillard, M. Enantiomer 1997, 2, 303 and references cited therein.
9. See also: Toyota, S.; Yasutomi, A.; Oki, M. Tetrahedron Lett. 1995, 36, 6297.
10. (a) Bijvoet, J. M.; Peerdeman, A. F.; van Bommel, A. J. Nature 1951, 168, 271.
11. (b) Bijvoet, J. M.; Peerdeman, A. F. Acta Crystallogr. 1956, 9, 1012 and references cited therein.
12. See also: Ibers, J.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781.
13. Stewart, J. J. P. MOPAC 93; Fujitsu Limited: Tokyo, Japan. 1993.
14. For definition of enantiomer by using CD data, see: Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H.; Okamoto, Y.; Yuki, H.; Kawada, Y. J. Chem. Soc., Perkin. Trans. 1 1985, 1845. Harada, N. Enantiomer 1996, 1, 81.
15. For definition of enantiomer by using CD data, see: Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H.; Okamoto, Y.; Yuki, H.; Kawada, Y. J. Chem. Soc., Perkin. Trans. 1 1985, 1845. Harada, N. Enantiomer 1996, 1, 81.
16. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, and Oxford University Press: Oxford, 1983.