Self-mediated stereoselective oxidation of thia-capped cyclodextrins

Angewandte Chemie - International Edition

Volumn 48, Issue 25, 2009, Pages 4555-4558

  Armspach, Dominique ^a   Matt, Dominique ^a   Toupet, Loic ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Cyclodextrins; Oxidation; Stereoselectivity; Sulfoxides; Supramolecular chemistry

Indexed keywords

INCLUSION COMPLEX; M-CHLOROPEROXYBENZOIC ACIDS; ORGANIC MEDIA; STEREOSELECTIVE OXIDATIONS; SULFOXIDES;

CYCLODEXTRINS; MACROMOLECULES; OXIDATION; STEREOSELECTIVITY; SUPRAMOLECULAR CHEMISTRY;

SILANES;

EID: 70349971401     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901200     Document Type: Article

References (38)

1. G. Wenz. Angew. Chem. 1994. 706, 851-870;
2. Angew. Chem. Int. Ed. Engl. 1994. 33. 803-822.
3. R. Breslow. Acc. Chem. Res. 1995, 28,146-153.
4. J. Szejtli, Chem. Rev. 1998, 98,1743-1754.
5. W. Saenger, J. Jacob, K. Gessler, T. Steiner, D. Hoffmann, H. Sanbe, K. Koizumi, S. M. Smith, T. Takaha, Chem. Rev. 1998, 98, 1787-1802.
6. E. Engeldinger, D. Armspach, D. Matt. Chem. Rev. 2003, 103, 4147-4174.
7. R. Villalonga, R. Cao, A. Fragoso, Chem. Rev. 2007,107, SOSS3116.
8. A. R. Khan, P. Forgo, K. J. Stine, V T. D'Souza, Chem. Rev. 1998, 98,1977-1996.
9. D. Armspach, D. Matt, Carbohydr. Res 1998, 310, 129-133.
10. C. J. Easton, S. F. Lincoln, Modified Cyclodextrins: Scaffolds and Templates for Supramolecular Chemistry, Imperial College Press, London, 1999.
11. A. J. Pearce, P. Sinay, Angew. Chem 2000, 112, 3756-3758;
12. Angew. Chem. Int. Ed. 2000, 39, 3610-3612.
13. D-Q. Yuan, Y. Kitagawa, K. Aoyama, T. Douke, M. Fukudome, K. Fujita, Angew. Chem. 2007, 119, 5112-5115;
14. Angew. Chem. Int. Ed. 2007, 46, 5024-5027.
15. M. Sollogoub, Eur. J. Org. Chem, 2009,1295-1303.
16. K. Takahashi, Chem. Rev. 1998, 98, 2013-2034.
17. A. Ueno. R. Breslow, Tetrahedron Lett. 1982, 23, 3451-3454.
18. A. G. Meyer, C J. Easton, S. F. Lincoln, G. W. Simpson, Chem. Commun. 1997,1517-1518.
19. CJ. Easton, Pure Appl. Chem. 2005, 77,1865-1871.
20. The stereochemistry of the pseudo-chiral sulfur atoms was assigned by giving arbitrarily priority to glucose unit A over glucose units B or C
21. D. Madec, F. Mingoia, C Macovei, G. Maitro, G. Giambastiani, G. Poli, Eur. J. Org. Chem. 2005. 552-557.
22. J.-P. Goddard, C Gomez, F. Brebion, S. Beauvière, L. Fensterbank, M. Malacria, Chem. Commun. 2007, 2929-2931.
23. G. Solladié, Synthesis 1981, 185-196.
24. G. Solladié, Pure Appl. Chem. 1988, 60, 1699-1704.
25. G. H. Posner, Acc. Chem. Res. 1987, 20, 72-78.
26. I. Fernández. N. Khiar, Chem. Rev. 2003, 103, 3651-3706.
27. C Carreño, G. Hernández-Torres, A. Urbano, F. Colobert. Eur. J. Org. Chem 2008,2035-2038.
28. K. Watanabe, T. Hirasawa, K. Hiroi, Chem. Pharm. Butt. 2002, 50,372-379.
29. G. Mestroni, E. Alessio, G. Sava. S. Pacor, M. Coluccia. A. Boccarelli, Met.-Based Drugs 1994. 7, 41-63.
30. M. C Carreño, Chem. Rev. 1995. 95, 1717-1760.
31. H.Sakuraba,K.Natori.Y.Tanaka,.J. Org. Chem. 1991,56, 41244129.
32. M. Bonchio, T. Carofiglio, F. Di Furia, R. Fornasíer, J. Org. Chem. 1995, 60, 5986-5988.
33. endo are reported herein.
34. D. Cremer, J. A. Pople.J. Am. Chem. Soc. 1975, 97, 1354-1358.
35. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Conformational nomenclature for five- and six-membered ring forms of monosaccharides and their derivatives (Recommendations 1980). Pure Appl. Chem. 1981, 53, 19011905.
36. M. V Rekharsky, Y. Inoue, Chem Rev. 1998, 98,1875-1917.
37. The anomeric signals in the 1H NMR spectra of the distorted AC thia-capped CDs 2 and 4 are spread out over a range of δ = 0.80 ppm and δ = 0.87 ppm, respectively, whereas those of circular shaped AB- thia-capped CDs 1 and 3 resonate within much narrower windows (δ = 0.07 ppm and δ = 0.23 ppm, respectively).
38. No such noncovalent bonds were found with the e.w-sulfoxide products.