A new ruthenium(II) chiroporphyrin containing a multipoint recognition site: Enantioselective receptor of chiral aliphatic alcohols

Inorganic Chemistry

Volumn 35, Issue 13, 1996, Pages 3733-3734

  Mazzanti, Marinella ^a   Veyrat, Marc ^a   Ramasseul, René ^a   Marchon, Jean Claude ^a   Turowska Tyrk, Ilona ^b   Shang, Maoyu ^b   Scheidt, W Robert ^b  

^a CEA GRENOBLE   (France)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013593532     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic960016j     Document Type: Article

References (28)

1. (a) Collman, J P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404.
2. (b) Naruta, Y. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed., Marcel Dekker: New York, 1994: p241.
3. (g) Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Sue. 1995, 117, 10950;
4. (h) Le Maux, P.; Bahri, H.; Simonneaux, G. J. Chem. Soc., Chem. Commun. 1991, 1350. Additional references are supplied in the Supporting Information.
5. (e) Molecular Recognition (Tetrahedron Symposia No. 56). Hamilton, A. D., Ed.; Tetrahedron 1995, 51. Additional references are supplied in the Supporting Information.
6. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
7. Veyrat, M.; Maury, O.; Faverjon, F.; Over, D. E.; Ramasseul, R.; Marchon, J. C.; Turowska -Tyrk, I;. Scheidt, W. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 220.
8. Bakshi, D.; Mahidroo, V. K.; Soman, R.; Dev, S. Tetrahedron 1989, 45, 767.
9. This compound was obtained in 71% overall yield and >99% diastereomeric purity from its precursor (lR)-cis-hemicaronaldehyde ("biocartol") by an improved procedure described in the Supporting Information.
10. Yield: 4% of 1.
11. (a) Analytical data for 2 are supplied in the Supporting Information,
12. (b) Le Maux, P.; Bahri, H.; Simonneaux, G. Tetrahedron 1993, 49. 1401
13. (c) Le Maux, P.; Bahri, H.; Simonneaux, G.; Toupet, L Inorg. Chem. 1995, 34,4691.
14. 2 = 0.184 for all 5474 data.
15. Sheldrick, G. M. SHELX93 Program for the Refinement of Crystal Structures. University of Gottingen, Germany, 1994.
16. (a) Flack, H. D. Acta Crystallogr., Sect. A 1983, 39, 876.
17. (b) Bernardelli, G.; Flack, H. D. Ibid. 1985, 41, 500.
18. Bonnet, J. J.; Eaton, S. S.; Eaton, G. R.; Holm, R. H.; Ibers, J. A. J. Am. Chem. Soc. 1973, 95, 2141.
19. (a) Hamilton, W. C.; Ibers, J. A. Hydrogen Bonding in Solids: W. A. Benjamin: New York, 1968; p 182.
20. (b) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
21. See comment in the Supporting Information.
22. James, B. R.; Pacheco, A.; Rettig, S. J.; Ibers, J. A. Inorg. Chem. 1988, 27, 2414. See comment in the Supporting Information.
23. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds: Wiley: New York, 1994; p 469.
24. See comment in the Supporting Information.
25. Pirkle, W. H.; Welch, C. J. Tetrahedron. Asymmetry 1994, 5, 777.
26. (a) Gaudemer, A.; Gaudemer, F.; Merienne, C. Org. Magn. Reson. 1983, 21, 83.
27. (b) Abraham, R. J.; Plant. J.; Bedford, G. R ; Wright, B Ibid. 1984, 22, 57.
28. (c) Abraham, R J.; Medforth, C. J. Magn. Reson. Chem. 1990, 28, 343.