Transfer hydrogenation of activated ketones using novel chiral Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 535-537

  Šterk, Damjan ^a   Stephan, Massoud S ^b   Mohar, Barbara ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b PhosPhoenix SARL   (France)

Author keywords

Asymmetric catalysis; Ketones; Ligands; Ruthenium; Transfer hydrogenation

Indexed keywords

ESTER; ETHYLENEDIAMINE DERIVATIVE; KETONE; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; DRUG DELIVERY SYSTEM; ENANTIOSELECTIVITY; HYDROGENATION; REDUCTION;

EID: 0345732575     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.201     Document Type: Article

References (20)

1. Sheldon R.A. Chirotechnology. 1993;Marcel Dekker, New York.
2. ′-dimethyl-DPEN: Gamez P., Fache F., Lemaire M. Tetrahedron: Asymmetry. 6:1995;705-718.
3. (a) . For reviews, see: Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051-1069
4. (b) Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97-102
5. (c) Palmer M.J., Wills M. Tetrahedron: Asymmetry. 10:1999;2045-2061
6. (d) Ohkuma T., Noyori R. Hydrogenation of Carbonyl Groups. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis I. 1999;199-246 Springer.
7. (a) . For Noyori's Ts-DPEN ligand, see: Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562-7563
8. (b) Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521-2522.
9. For Ts-DPEN enclosed dendritic ligands, see: Chen Y.-C., Wu T.-F., Deng J.-G., Liu H., Cui X., Zhu J., Jiang Y.-Z., Choi M.C.K., Chan A.S.C. J. Org. Chem. 67:2002;5301-5306.
10. For polymer-supported Ts-DPEN ligand, see: Bayston D.J., Travers C.B., Polywka M.E.C. Tetrahedron: Asymmetry. 9:1998;2015-2018.
11. 2-DPEN ligand, see: Meuzelaar G.J., van Vliet M.C.A., Maat L., Sheldon R.A. Eur. J. Org. Chem. 9:1999;2315-2321.
12. 2-DPEN ligands, see: Bubert C., Blacker J., Brown S.M., Crosby J., Fitzjohn S., Muxworthy J.P., Thorpe T., Williams J.M.J. Tetrahedron Lett. 42:2001;4037-4039.
13. (a) Mohar B., Valleix A., Desmurs J.-R., Felemez M., Wagner A., Mioskowski C. Chem. Commun. 2001;2572-2573
14. (b) Taran F., Gauchet C., Mohar B., Meunier S., Valleix A., Renard P.Y., Crémion C., Grassi J., Wagner A., Mioskowski C. Angew. Chem. Int. Ed. 41:2002;124-127.
15. Šterk D., Stephan M.S., Mohar B. Tetrahedron: Asymmetry. 13:2002;2605-2608.
16. Yamakawa M., Ito H., Noyori R. J. Am. Chem. Soc. 122:2000;1466-1478.
17. (a) . α-Keto esters were prepared according to: Nimitz J.S., Mosher H.S. J. Org. Chem. 46:1981;211-213
18. (b) Takao, T. S.; Takashi, M. T.; Hisashi, T. O.; Hiromu, K. S. GB 1 533 491, 1978;
19. (c) Domagala J.M. Tetrahedron Lett. 21:1980;4997-5000.
20. 2; J 3.2 Hz), 4.76 (d, 1H, CHNH; J 3.2 Hz), 6.98-7.42 (m, 10H, 2 × Ph), 7.64 (d, 1H, H-3; J 8.6 Hz), 8.08 (dd, 1H, H-5; J 8.6, 2.1 Hz), 8.45 (d, 1H, H-6; J 2.1 Hz).