Enantiomeric resolution of a ruffled porphyrinoid

Angewandte Chemie - International Edition

Volumn 43, Issue 13, 2004, Pages 1688-1691

  Daniell, Heather W ^a   Brückner, Christian ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

Chirality; Conformation analysis; Nickel; Porphyrinoids

Indexed keywords

CHOLESTEROL; CHROMOPHORES; ETHANOL; NICKEL; REACTION KINETICS;

DIASTEREOMERS; ENANTIOMERIC RESOLUTION; PORPHYRINIC CHROMOPHORE;

PORPHYRINS;

CHOLESTEROL; MACROCYCLIC COMPOUND; NICKEL; POPHYRINOID; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOPHORE; DIASTEREOISOMER; ENANTIOMER;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICKEL; ORGANOMETALLIC COMPOUNDS; PORPHYRINS; STEREOISOMERISM;

EID: 2942654430     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352970     Document Type: Article

References (29)

1. H. Ogoshi, T. Mizutani, T. Hayashi, Y. Kuroda in Porphyrin Handbook, Vol. 6 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 279-340.
2. a) J.-C. Marchon, R. Ramasseul in Porphyrin Handbook, Vol. 11 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2003, pp. 75-132;
3. b) G. Simonneaux, P. Le Maux, Coord. Chem. Rev. 2002, 228, 43-60.
4. See, for example: a) H. Nakagawa, T. Nagano, T. Higuchi, Org. Lett. 2001, 3, 1805-1807;
5. b) B. Boitrel, Baveux-Chambenoît, P. Richard, Eur. J. Org. Chem. 2001, 4213-4221.
6. a) Y. Furusho, T. Kimura, Y. Mizuno, T. Aida, J. Am. Chem. Soc. 1997, 119, 5267-5268;
7. b) E. Bellacchio, R. Lauceri, S. Gurrieri, L. M. Scolaro, A. Romeo, R. Purrello, J. Am. Chem. Soc. 1998, 120, 12353-12354;
8. c) Y. Kubo, T. Ohno, J. Yamanaka, S. Tokita, T. Iida, Y. Ishimaru, J. Am. Chem. Soc. 2001, 123, 12700-12701, Y. Mizuno, T. Aida, K. Yamaguchi, J. Am. Chem. Soc. 2000, 122, 5278-5285.
9. c) Y. Kubo, T. Ohno, J. Yamanaka, S. Tokita, T. Iida, Y. Ishimaru, J. Am. Chem. Soc. 2001, 123, 12700-12701, Y. Mizuno, T. Aida, K. Yamaguchi, J. Am. Chem. Soc. 2000, 122, 5278-5285.
10. For chiral porphyrin-based entities involving two or more covalently or noncovalently linked porphyrins, see: a) T. S. Balaban, A. D. Bhise, M. Fischer, M. Linke-Schaetzel, C. Roussel, N. Vanthuyne, Angew. Chem. 2003, 115, 2190-2194; Angew. Chem. Int. Ed. 2003, 42, 2140-2144;
11. For chiral porphyrin-based entities involving two or more covalently or noncovalently linked porphyrins, see: a) T. S. Balaban, A. D. Bhise, M. Fischer, M. Linke-Schaetzel, C. Roussel, N. Vanthuyne, Angew. Chem. 2003, 115, 2190-2194; Angew. Chem. Int. Ed. 2003, 42, 2140-2144;
12. b) V. V. Borovkov, J. M. Lintuluoto, G. A. Hembury, M. Sugiura, R. Arakawa, Y. Inoue, J. Org. Chem. 2003, 68, 7176-7192;
13. c) B. Boitrel, V. Baveux-Chambenoit, R. Philippe, Eur. J. Inorg. Chem. 2003, 7, 1666-1672;
14. d) Y. Mizuno, T. Aida, Chem. Commun. 2003, 20-21;
15. e) T. Hayashi, T. Aya, M. Nonoguchi, T. Mizutani, Y. Hisaeda, S. Kitagawa, H. Ogoshi, Tetrahedron 2002, 58, 2803-2811.
16. a) J. R. McCarthy, H. A. Jenkins, C. Brückner, Org. Lett. 2003, 5, 19-22;
17. b) C. Brückner, S. J. Rettig, D. Dolphin, J. Org. Chem. 1998, 63, 2094-2098.
18. C. J. Campbell, J. F. Rusling, C. Brückner, J. Am. Chem. Soc. 2000, 122, 6679-6685.
19. C. Brückner, E. D. Sternberg, J. K. MacAlpine, S. J. Rettig, D. Dolphin, J. Am. Chem. Soc. 1999, 121, 2609-2610.
20. 3-hybridized centers with respect to the twofold rotational axis of the chromophore), two pairs of the eight posible isomers are identical.
21. For a detailed description of the experimental details, see the Supporting Information.
22. We have not been able to assign the absolute stereochemistry of the two enantiomeric chromophores (R)-4 and (S)-4. In all the experiments, we have used (+)-cholesterol. Herein the chromophores will be identified by their characteristic features in their CD-spectra, that is, 4(+ 443)-Chol is the isomer with a positive Cotton effect at 443 nm and 4(-443)-Chol the corresponding diastereomer with a negative Cotton affect at this wavelength.
23. a) L. Barloy, D. Dolphin, D. Dupré, T. P. J. Wijesekera, J. Org. Chem. 1994, 59, 7976-7985;
24. b) J. R. McCarthy, M. A. Hyland, C. Brückner, Chem. Commun. 2003, 1738-1739.
25. Molecular modeling (Quantum CAChe 4.9, Fujitsu, 2002; MM3 force field) also predicts the anti-configuration.
26. Cholesterol has no absorption in the wavelength range 350-750 nm.
27. Techniques currently investigated to determine the absolute stereochemistry of the conformers: X-ray structure determination; vibrational optical activity: L. A. Nafie, T. B. Freedman in Circular Dichroism, 2nd ed. (Eds.: N. Berova, K. Nakanishi, R. W. Woody), Wiley-VCH, New York, 2000, pp. 97-131.
28. J. K. M. Sanders, N. Bampos, Z. Clyde-Watson, S. L. Darling, J. C. Hawley, H.-J. Kim, C. C. Mak, S. Webb, The Porphyrin Handbook, Vol. 3 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 1-48.
29. J. R. McCarthy, P. J. Melfi, S. H. Capetta, C. Brückner, Tetrahedron 2003, 59, 9137-9146.