Asymmetric transfer hydrogenation of aromatic ketones with the ruthenium(II) catalyst derived from C2 symmetric N,N′-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide

Journal of Organometallic Chemistry

Volumn 695, Issue 9, 2010, Pages 1392-1398

  Aydemir, Murat ^a   Meriç, Nermin ^a   Durap, Feyyaz ^a   Baysal, Akin ^a   Toǧrul, Mahmut ^a  

^a DICLE UNIVERSITY   (Turkey)

Author keywords

Asymmetric transfer hydrogenation; Catalysis; Chiral phosphinite; Complexes; Ruthenium

Indexed keywords

ACETOPHENONES; ARGON ATMOSPHERES; AROMATIC KETONES; ASYMMETRIC TRANSFER HYDROGENATION; CATALYTIC REACTIVITY; CHIRAL ALCOHOLS; ELEMENTAL SULFUR; FTIR SPECTROSCOPY; MOLECULAR CATALYSTS; ORGANIC SYNTHESIS; P-CYMENE; PHOSPHINITES; RU COMPLEXES; RUTHENIUM COMPLEXES; SELENIDES;

ARGON; CATALYSIS; CATALYSTS; HYDROGEN PEROXIDE; HYDROGEN SULFIDE; HYDROGENATION; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PALLADIUM; PALLADIUM COMPOUNDS; PLATINUM; PLATINUM COMPOUNDS; RUTHENIUM; SELENIUM; SULFUR; SYNTHESIS (CHEMICAL); TOLUENE;

RUTHENIUM COMPOUNDS;

EID: 77950188141     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.02.003     Document Type: Article

References (50)

1. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis (1999), Springer, Berlin
2. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. second ed. (2000), John Wiley and Sons, New York
3. Lin G.-Q., Li Y.-M., and Chan A.S.C. Principles and Applications of Asymmetric Synthesis (2001), Wiley & Sons, New York
4. Zhang S.Y., and Guo J.Q. Asymmetric Catalysis-Principle and Application in Organic Synthesis (2002), Science Press, Beijing p. 27
5. Ohkuma T., Ooka H., Hashiguchi S., Ikariya T., and Noyori R. J. Am. Chem. Soc. 117 (1995) 2675-2676
6. Ohkuma T., Ooka H., Hashiguchi S., Ikariya T., and Noyori R. J. Am. Chem. Soc. 117 (1995) 10417-10418
7. Ohkuma T., Koizumi M., Doucet H., Pham T., Kozawa M., Murata K., Katayama E., Yokozawa T., Ikariya T., and Noyori R. J. Am. Chem. Soc. 120 (1998) 13529-13530
8. Hashiguchi S., Fujii A., Takehara J., Ikariya T., and Noyori R. J. Am. Chem. Soc. 117 (1995) 7562-7563
9. Takehara J., Hashiguchi S., Fujii A., Inoue S., Ikariya T., and Noyori R. J. Chem. Soc., Chem. Commun. (1996) 233-234
10. Galka P.W., and Kraatz H.-B. J. Organomet. Chem. 674 (2003) 24-31
11. Knowles W.S. Acc. Chem. Res. 16 (1983) 106-112
12. Noyori R., and Takaya H. Acc. Chem. Res. 23 (1990) 345-350
13. Noyori R. Science 248 (1990) 1194-1199
14. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., and Noyori R. J. Am. Chem. Soc. 102 (1980) 7932-7934
15. MacKay C.A., and Vedejs E. J. Org. Chem. 71 (2006) 498-503
16. Shi M., Chen L.-H., and Li C.-Q. J. Am. Chem. Soc. 127 (2005) 3790-3800
17. Ogasawara M., Ngo H.L., Sakamoto T., Takahashi T., and Lin W. Org. Lett. (2005) 2881-2884
18. Kinoshita N., Marx K.H., Tanaka K., Tsubaki K., Kawabata T., Yoshikai N., Nakamura E., and Fuji K. J. Org. Chem. 69 (2004) 7960-7964
19. Hauptman E., Shapiro R., and Marshall W. Organometallics (1998) 4976-4982
20. Shin S., and RajanBabu T.V. Org. Lett. 1 (1999) 1229-1232
21. Guo R.W., Elpelt C., Chen X., Song D., and Morris R.H. Chem. Commun. (2005) 3050-3052
22. Buono G., Siv C., Peiffer G., Triantaphlides C., Denis P., Mortreux A., and Petit F. J. Org. Chem. 50 (1985) 1781-1782
23. Agbossou F., Carpentier J.-F., Hapiot F., Suisse I., and Mortreux A. Coord. Chem. Rev. 178-180 (1998) 1615-1645
24. Pasquier C., Naili S., Mortreux A., Agbossou F., Plinski L., Brocard J., Eilers J., Reiners I., Peper V., and Martens J. Organometallics 19 (2000) 5723-5732
25. Ojima I., Clos N., and Bastos C. Tetrahedron 45 (1989) 6901-6939
26. Kotha S. Tetrahedron 50 (1994) 3639-3662
27. Akutagawa S. Appl. Catal., A 128 (1995)
28. Roucoux A., Thieffry L., Carpentier J.-F., Devocelle M., Meliet C., Agbossou F., and Mortreux A. Organometallics 15 (1996) 2440-2449
29. Whitesell J.K. Chem. Rev. 89 (1989) 1581-1590
30. Blaser H.-U., Malan C., Pugin B., Spindler F., Steiner H., and Studer M. Adv. Synth. Catal. 345 (2003) 103-151
31. Dang T.P., and Kagan H.B. Chem. Commun. (1971) 481-487
32. Inoguchi K., Sakuraba S., and Achiwa K. Synlett (1992) 169-178
33. Sunkur M., Baris D., Hosgoren H., and Togrul M. J. Org. Chem. 73 (2008) 2570-2575
34. Baysal A., Aydemir M., Durap F., Gümgüm B., Özkar S., and Yildirim L.T. Polyhedron 26 (2007) 3373-3378
35. Fei Z., Scopelliti R., and Dyson P.J. Eur. J. Inorg. Chem. (2004) 530-537
36. Aydemir M., Baysal A., Öztürk G., and Gümgüm B. Appl. Organomet. Chem. 23 (2009) 108-113
37. Slawin A.M.Z., Wheatley J., Wheatley M.V., and Woollins J.D. Polyhedron 22 (2003) 1397-1405
38. Balakrishna M.S., George P.P., and Mobin S.M. Polyhedron 24 (2005) 475-480
39. Fei Z., Scopelliti R., and Dyson P.J. Inorg. Chem. 42 (2003) 2125-2130
40. Zhang Q., Hua G., Bhattacharyya P., Slawin A.M.Z., and Woollins J.D. J. Chem. Soc., Dalton Trans. (2003) 3250-3257
41. Francio G., Arena C.G., Panzalorto M., Bruno G., and Faraone F. Inorg. Chim. Acta 277 (1998) 119-126
42. Balakrishna M.S., Krishnamurthy S.S., Murugavel R., Netaji M., and Mathews I.I. J. Chem. Soc., Dalton Trans. (1993) 477-482
43. Biricik N., Durap F., Gümgüm B., Fei Z., and Scopelliti R. Trans. Met. Chem. 32 (2007) 877-883
44. Aydemir M., Baysal A., and Gümgüm B. J. Organomet. Chem. 693 (2008) 3810-3814
45. Tribo R., Munoz S., Pons J., Yanez R., Alvarez-Larena A., Piniella J.F., and Ros J. J. Organomet. Chem. 690 (2005) 4072-4079
46. Aydemir M., Baysal A., Meric N., and Gümgüm B. J. Organomet. Chem. 694 (2009) 2488-2492
47. Ceron-Camacho R., Gomez-Benitez V., Lagadec R.L., Morales-Morales D., and Toscano R.A. J. Mol. Catal. A: Chem. 247 (2006) 124-129
48. Reetz M.T., and Li X. J. Am. Chem. Soc. 128 (2006) 1044-1045
49. Drew D., Doyle J.R., and Shaver A.G. Inorg. Synth. 13 (1972) 47-55
50. McDermott J.X., White J.F., and Whitesides G.M. J. Am. Chem. Soc. 98 (1976) 6521-6528