Dicarbonylchloro(pentabenzylcyclopentadienyl)rutheniuni as racemization catalyst in the dynamic kinetic resolution of secondary alcohols

European Journal of Organic Chemistry

Volumn , Issue 9, 2009, Pages 1317-1320

  Mavrynsky, Denys ^a   Päiviö, Mari ^b   Lundell, Katri ^b   Sillanpää, Reijo ^c   Kanerva, Liisa T ^b   Leino, Reko ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b UNIVERSITY OF TURKU   (Finland)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Cyclopentadienyl ligands; Dynamic kinetic resolution; Enzyme catalysis; Racemization; Ruthenium

Indexed keywords

EID: 63449122180     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801248     Document Type: Article

References (19)

1. P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623-7626.
2. a) A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. Int. Ed. Engl. 1997, 36, 1211-1212;
3. b) B. A. Persson, A. L. E. Larsson, M. Le Ray, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 1645-1650.
4. For reviews, see: a) O. Pàmies, J.-E. Bäckvall, Chem. Rev. 2003, 103, 3247-3262;
5. b) B. Martín-Matute, J.-E. Bäckvall, Curr. Opin. Chem. Biol. 2007, 11, 226-232.
6. Y. Ahn, S.-B. Ko, M.-J. Kim, J. Park, Coord. Chem, Rev. 2008, 252, 647-658.
7. B. Martin-Matute, M. Edin, K. Bogár, F. B. Kaynak, J.-E. Bäckvall, J. Am. Chem. Soc. 2005, 127, 8817-8825.
8. a) J. H. Choi, Y. H. Kim, S. H. Nam, S. T. Shin, M.-J. Kim, J. Park, Angew. Chem, Int. Ed. 2002, 41, 2373-2376;
9. b) J. H. Choi, Y. K. Choi, Y. H. Kim, E. S. Park, E. J. Kim, M.-J. Kim, J. Park, J. Org. Chem. 2004, 69, 1972-1977.
10. a) C.P Casey, S. W. Singer, D. R. Powell, P. K. Hayashi, M. Kavan, J. Am. Chem. Soc. 2001, 123, 1090-1100;
11. b) G. Csjernvik, A. H. Eu, L. Fadini, B. Pugin, J.-E. Bäckvall, J. Org. Chem. 2002, 67, 1657-1662.
12. D. Mavrynsky, R. Sillanpää, R. Leino, Organometallics 2009, 28, 589-605.
13. R. M. Bullock, P. J. Fagan, E, M. Hauptman (DuPont), PCT Int. Appl. 2001, WO 01/98241 A2.
14. W.-M. Tsai, M. D. Rausch, R. D. Rogers, Organometallics 1996, 15, 2591-2594.
15. S. Namorado, M. A. Antunes, L. F. Veiros, J. R. Ascenso, M. T. Duarte, A. M. Martins, Organometallics 2008, 27, 4589-4599.
16. J. W. Chambers, A. J. Baskar, S. G. Bott, J. L. Atwood, M. D. Rausch, Organometallics 1986, 5, 1635-1641.
17. The molecular structure of 5c shows a disorder, in which the Cl ligand and one of the two CO ligands have two orientations in a 1:1 ratio. In Figure 5, only one orientation of the disordered ligands is shown. For a more detailed illustration, see Supporting Information.
18. L. Veum, U. Hanefeld, Tetrahedron: Asymmetry 2004, 15, 3707-3709.
19. L. Veum, L. T. Kanerva, P. J. Hailing, T. Maschmeyer, U. Hanefeld, Adv. Synth. Calcd. 2005, 347, 1015-1021.