Supramolecular Chirogenesis in Bis(zinc porphyrin): An Absolute Configuration Probe Highly Sensitive to Guest Structure

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1565-1568

  Borovkov, Victor V ^a   Lintuluoto, Juha M ^a   Inoue, Yoshihisa ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001422162     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0000556     Document Type: Article

References (23)

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12. Determination of the absolute configuration of chiral compounds: (a) Baum, G.; Constable, E. C.; Fenske, D.; Housecraft, C. E.; Kulke, T. Chem. Eur. J. 1999, 5, 1862-1873. (b) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (c) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359. (d) Kikuchi, Y.; Kobayashi, K.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 1351-1358.
13. Determination of the absolute configuration of chiral compounds: (a) Baum, G.; Constable, E. C.; Fenske, D.; Housecraft, C. E.; Kulke, T. Chem. Eur. J. 1999, 5, 1862-1873. (b) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (c) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359. (d) Kikuchi, Y.; Kobayashi, K.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 1351-1358.
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15. Borovkov, V. V.; Lintuluoto, J. M.; Fujiki, M.; Inoue, Y. J. Am. Chem. Soc., in press.
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20. These two transitions are the major contributors to the observed Soret band. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371-392.
21. 2. The detailed conformational analysis and contribution of other conformations to the chirality induction process will be reported elsewhere. However, preliminary results obtained for monomeric zinc octaethylporphyrin binding with chiral ligands show that the total intensity of the CD signals may contain a minor contribution (up to 10%) from the point chirality due to the direct zinc porphyrin-ligand interactions.
22. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy. Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
23. For Δε and ε values at 193 K, see ref 7.