A CD method for determination of the absolute stereochemistry of acyclic glycols. 2. Application of the CD exciton chirality method to acyclic 1,2-dibenzoates systems

Enantiomer

Volumn 1, Issue 2, 1996, Pages 119-138

  Harada, Nobuyuki ^a   Saito, Akira ^a   Ono, Hiroshi ^a   Murai, Shinji ^a   Li, Hong Yu ^a   Gawronski, Jacek ^b   Gawronska, Krystyna ^b   Sugioka, Tatsuo ^c   Uda, Hisashi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

^c SANOFI   (France)

Author keywords

Absolute configuration; Acyclic 1,2 dibenzoates; CD exciton chirality method; Chiral acyclic 1,2 glycols; Exciton split CD Cotton effects

Indexed keywords

EID: 0000548931     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, Calif., and Oxford University Press, Oxford, 1983.
2. N. Harada, A. Saito, H. Ono, J. Gawronski, K. Gawronska, T. Sugioka, H. Uda, and T. Kuriki, J. Am. Chem. Soc., 1991, 113, 3842-3850.
3. J. Gawronski, K. Gawronska, and U. Rychlewska, Tetrahedron Lett., 1989, 30, 6071-6074.
4. Y. Yamamoto, M. Fushimi, J. Oda, and Y. Inoue, Agric. Biol. Chem., 1975, 39, 2223-2226.
5. H. Uzawa, Y. Nishida, S. Kanada, H. Ohrui, and H. Meguro, J. Chem. Soc., Chem. Commun., 1989, 862-863.
6. H. Uzawa, Y. Nishida, H. Ohrui, and H. Meguro, J. Org. Chem., 1990, 55, 116-122.
7. W. Wiesler and K. Nakanishi, J. Am. Chem. Soc., 1989, 111, 3446-3447.
8. W. Wiesler and K. Nakanishi, J. Am. Chem. Soc., 1989, 111, 9205-9213.
9. P. Zhou, N. Zhao, D. N. Rele, N. Berova, and K. Nakanishi, J. Am. Chem. Soc., 1993, 115, 9313-9314.
10. Y. Mori, Y. Kohchi, M. Suzuki, and H. Furukawa, J. Am. Chem. Soc., 1992, 114, 3557-3559.
11. Y. Mori, Y. Kohchi, M. Suzuki, and H. Furukawa, Tetrahedron Lett., 1992, 33, 2029-2030.
12. Y. Mori and H. Furukawa, Tetrahedron, 1995, 51, 6725-6738.
13. It should be noted that the R and S notation of the chirality does not directly reflect the dibenzoate exciton chirality. Therefore the R and S notation is useless in this case. For example, dibenzoates (2S)-1a-3d exhibit positive first and negative second Cotton effects, respectively, while (2S,3S)-4b does negative first and positive second Cotton effects (Table II).
14. N. Nakagawa and Y. Arata, in Chemical Society of Japan (edited), Jikken Kagaku Koza (Zoku), Maruzen, Tokyo, 1967, vol 12 (NMR), 100-101 pp.
15. S. Takano and K. Ogasawara, J. Synthet. Org. Chem., Jpn., 1987, 45, 1157-1170, and references cited therein.
16. V. Schurig, B. Koppenhoefer, and W. Buerkle, J. Org. Chem., 1980, 45, 538-541.
17. L. J. Rubin, H. A. Landy, and O. L. Fischer, J. Am. Chem. Soc., 1952, 74, 425-428.
18. M. Carmack and C. J. Kelley, J. Org. Chem., 1968, 33, 2171-2173.
19. P. W. Feit, J. Med. Chem., 1964, 7, 14-17.