Sweets for catalysis - Facile optimisation of carbohydrate-based bis(oxazoline) ligands

European Journal of Organic Chemistry

Volumn , Issue 7, 2009, Pages 997-1008

  Minuth, Tobias ^a   Irmak, Mustafa ^a   Groschner, Annika ^b   Lehnert, Tobias ^a   Boysen, Mike M K ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Asymmetric catalysis; Carbohydrates; Ligand design; N ligands

Indexed keywords

EID: 61849118917     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801035     Document Type: Article

References (35)

1. For early examples of carbohydrate-based complex ligands, see: a) W. R. Cullen, Y. Sugi, Tetrahedron Lett. 1978, 19, 1635-1636;
2. b) R. Jackson, D. J. Thompson, J. Organomet. Chem. 1978, 159, C29-C31;
3. c) R. Selke, React. Kinet. Catal. Lett. 1979, 10, 135-138;
4. d) D. Sinou, G. Descotes, React. Kinet. Catal. Lett. 1980, 14, 463-466;
5. e) R. Selke, J. Prakt. Chem. 1987, 329, 717-724.
6. a) M. Diéguez, C. Claver, O. Pàmies, Eur. J. Org. Chem. 2007, 4621-4634;
7. b) M. M. K. Boysen, Chem. Eur. J. 2007, 13, 8648-8659;
8. c) M. Dieguez, O. Pamies, C. Claver, Chem. Rev. 2004, 104, 3189-3215;
9. d) M. Diéguez, O. Pàmies, A. Ruiz, Y. Díaz, S. Castillón, C. Claver, Coord. Chem. Rev. 2004, 248, 2165-2192.
10. a) G. Desimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561-3651;
11. b) H. A. McManus, P.J. Guiry, Chem. Rev. 2004, 104, 4151-4202;
12. c) A. K. Ghosh, P. Mathivanan, J. Capiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
13. G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev. 2003, 103, 3119-3154.
14. For the first examples of carbohydrate mono(oxazoline)ligands, see: a) B. Gläser, H. Kunz, Synlett 1998, 53-54;
15. b) K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, Chem. Commun. 1999, 415-416;
16. c) Y. Mata, M. Diéguez, O. Pàmies, C. Claver, Org. Lett. 2005, 7, 5597-5599.
17. Ch. G. Hartinger, A. A. Nazarov, M. Galanski, M. Reithofer, B. K. Keppler, J. Organomet. Chem. 2005, 690, 3301-3308.
18. M. Irmak, A. Groschner, M. M. K. Boysen, Chem. Commun. 2007, 177-179.
19. M. Irmak, M. M. K. Boysen, Adv. Synth. Catal. 2008, 350, 403-405.
20. a) D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728;
21. b) R. E. Loewenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008.
22. a) H. Duddeck, Chem. Rec. 2005, 5, 396-409;
23. b) E. Díaz Gómez, J. Jios, C. O. Della Védova, H. D. March, H. E. Di Loreto, G. Tóth, A. Simon, D. Albert, S. Moeller, R. Wartchow, H. Duddeck, Tetrahedron: Asymmetry 2005, 16, 2285-2293.
24. B. Liberek, A. Melcer, A. Osuch, R. Wakieć, S. Milewski, A. Wiśniewski, Carbohydr. Res. 2005, 340, 1876-1884.
25. C. A. Wartchow, P. Wang, M. D. Bednarski, M. R. Callstrom, J. Org. Chem. 1995, 60, 2216-2226.
26. T. Minuth, M. M. K. Boysen, Synlett 2008, 1483-1486.
27. D. Crich, S. Sun, J. Am. Chem. Soc. 1997, 119, 11217-11223.
28. A. A. Sherman, O.N. Yudina, Y. V. Mironov, E. V. Sukhova, A. S. Shashkov, V. M. Menshov, N. E. Nifantiev, Carbohydr. Res. 2001, 336, 13-46.
29. M. Hederos, P. Konradsson, J. Carbohydr. Chem. 2005, 24, 297-320.
30. N. Khiar, B. Suárez, I. Fernández, Inorg. Chim. Acta 2006, 359, 3048-3053.
31. E. Bourgeaux, J.-C. Combret, Tetrahedron: Asymmetry 2000, 11, 4189-4205.
32. L. Huang, Z. Wang, X. Li, X. Ye, X. Huang, Carbohydr. Res. 2006, 341, 1669-1679.
33. L. Abrous, P. A. Jokiel, S. R. Friedrich, J. Hynes Jr, A. B. Smith III, R. J. Hirschmann, J. Org. Chem. 2004, 69, 280-302.
34. a) M. A. Nashed, C. W Slife, M. Kiso, L. Anderson, Carbohydr. Res. 1980, 82, 237-252;
35. b) C. Foces-Foces, F. H. Cano, M. Bernabe, S. Penades, M. Martin-Lomas, Carbohydr. Res. 1984, 135, 1-11.