New C2-symmetric chiral phosphinite ligands based on amino alcohol scaffolds and their use in the ruthenium-catalysed asymmetric transfer hydrogenation of aromatic ketones

Comptes Rendus Chimie

Volumn 16, Issue 4, 2013, Pages 363-371

  Durap, Feyyaz ^a   Aydemir, Murat ^a   Elma, Duygu ^a   Baysal, Akin ^a   Turgut, Yilmaz ^a  

^a DICLE UNIVERSITY   (Turkey)

Author keywords

Asymmetric transfer hydrogenation; C2 symmetry; Chiral phosphinite ligands; Homogeneous catalysis; Ruthenium

Indexed keywords

EID: 84876949345     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2012.12.003     Document Type: Article

References (62)

1. H.U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103
2. R. Noyori, and T. Ohkuma Angew. Chem. Int. Ed. Engl. 40 2001 40
3. V. Turcry, C. Pasquier, and F. Agbossou-Niedercorn C. R. Chimie 6 2003 179
4. T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikaria, and R. Noyori J. Am. Chem. Soc. 117 1995 2675
5. T. Ohkuma, H. Ooka, T. Ikaria, and R. Noyori J. Am. Chem. Soc. 117 1995 10417
6. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, T. Ikaria, and R. Noyori Angew. Chem. Int. Ed. 37 1998 1703
7. G. Zassinovich, G. Mestroni, and S. Gladiali Chem. Rev. 92 1992 1051
8. R. Noyori, and S. Hashiguchi Acc. Chem. Res. 30 1997 97
9. R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, and S. Akutagawa J. Am. Chem. Soc. 109 1987 5856
10. H. Shimizu, I. Nagasaki, and T. Satio Tetrahedron 61 2005 5405
11. A. Börner Phosphorus Ligands in Asymmetric Catalysis vol. 3 2008 Wiley-VCH Weinheim, Germany
12. R. Guo, C. Elpelt, X. Chen, D. Song, and R.H. Morris Chem. Commun. 2005 3050
13. I. Ojima, N. Clos, and C. Bastos Tetrahedron 45 1989 6901
14. S. Kotha Tetrahedron 50 1994 3639
15. S. Akutagawa App. Catal. A: Gen. 128 1995 171
16. A. Roucoux, L. Thieffry, J.F. Carpentier, M. Devocelle, C. Meliet, F. Agbossou, and A. Mortreux Organometallics 25 1996 2440
17. R.H. Crabtree The Organometallic Chemistry of the Transition Metals 2001 Wiley-Interscience New York
18. H.B. Kagan, and M. Sasaki Transition Metals for Organic Synthesis 1998 Wiley-VCH Weinheim
19. M.T. Reetz, and G. Mehler Angew. Chem. Int. Ed. 39 2000 3889
20. M. Aydemir, N. Meriç, F. Durap, A. Baysal, and M. Toǧrul J. Organomet. Chem. 695 2010 1392
21. M. Aydemir, A. Baysal, N. Meriç, C. Kayan, M. Toǧrul, and B. Gümgüm Appl. Organomet. Chem. 24 2010 215
22. M. Aydemir, N. Meriç, A. Baysal, B. Gümgüm, M. Toǧrul, and Y. Turgut Tetrahedron Asymmetr. 21 2010 703
23. D. Hobuß, J. Hasenjager, B. Driessen-Hölscher, A. Baro, K.V. Axenov, S. Laschat, and W. Frey Inorg. Chim. Acta 374 2011 94
24. P.W. Galka, and H.B. Kraatz J. Organomet. Chem. 674 2003 24
25. T.P. Dang, and H.B. Kagan Chem. Commun. 1971 481
26. K. Inoguchi, S. Sakuraba, and K. Achiwa Synlett 1992 169
27. S. Castillon, C. Claver, and Y. Diaz Chem. Soc. Rev. 34 2005 702
28. B. Jiang, and Y. Feng Tetrahedron Lett. 43 2002 2975
29. B. Jiang, Y. Feng, and J.F. Hang Tetrahedron Asymmetr. 12 2001 2323
30. X.W. Yang, J.H. Shen, C.S. Da, H.S. Wang, W. Su, D.X. Liu, R. Wang, C.K.C. Michael, and S.C.C. Albert Tetrahedron Lett. 42 2001 6573
31. C. Garcia, L.K. LaRochelle, and P.J. Walsh J. Am. Chem. Soc 124 2002 10970
32. M. Shi, and J.K. Jiang Tetrahedron Asymmetr. 10 1999 1673
33. T.H. Chan, and G.Z. Zheng Can. J. Chem. 75 1997 629
34. A. Pfaltz J.W. Drury III, PNAS 101 2004 5723
35. M.J. McKennon, and A.I. Meyers J. Org. Chem. 58 1993 3568
36. Y. Turgut, N. Demirel, and H. Hoşgören J. Inclus. Phenom. Macro. Chem. 54 2006 29
37. S. Özbey, H. Höşgören, Y. Turgut, and G. Topal J. Inclus. Phenom. Macro. Chem. 39 2001 315
38. Y. Turgut, and H. Hoşgören Tetrahedron Asymmetr. 14 2003 3815
39. M. Toǧrul, Y. Turgut, and H. Hoşgören Chirality 16 2004 351
40. A. Baysal, M. Aydemir, F. Durap, B. Gümgüm, S. Özkar, and L.T. Yildirim Polyhedron 26 2007 3373
41. Z. Fei, R. Scopelliti, and P.J. Dyson Eur. J. Inorg. Chem. 2004 530
42. R. Ceron-Camacho, V. Gomez-Benitez, R. Le Lagadec, D. Morales-Morales, and R.A. Toscano J. Mol. Catal. A 247 2006 124
43. E.A. Broger, W. Burkart, M. Hennig, M. Scalone, and R. Schmid Tetrahedron Asymmetr. 9 1998 4043
44. A. Bader, and E. Lindner Coord. Chem. Rev. 1991 27
45. R.L. Chowdhury, and J.E. Backvall J. Chem. Soc. Commun. 1991 1063
46. G. Venkatachalam, and R. Ramesh Inorg. Chem. Commun. 8 2005 1009
47. J.X. Gao, T. Ikariya, and R. Noyori Organometallics 15 1996 1087
48. Y. Kuroki, Y. Sakamaki, and K. Iseki Org. Lett. 3 2001 457
49. Y. Kuroki, D. Asada, Y. Sakamaki, and K. Iseki Org. Lett. 41 2000 4603
50. I. Nieto, M.S. Livings, J.B.III. Sacci, L.E. Reuther, M. Zeller, and E.T. Papish Organometallics 30 2011 6339
51. M.J. Palmer, and M. Will Tetrahedron Asymmetr. 1999 2045
52. E.P. Kelson, and P.P. Phengsy J. Chem. Soc. Dalton Trans. 2000 4023
53. J.E. Backwall J. Organomet. Chem. 652 2002 105
54. H. Zhang, B.C. Yang, Y.Y. Li, Z.R. Donga, J.X. Gao, H. Nakamura, K. Murata, and T. Ikariya J. Chem. Com. Chem. Commun. 2003 142
55. J.S. Chen, Y. Li, Z. Dong, B. Li, and J. Gao Tetrahedron Lett. 2004 8415
56. J. Hannedouche, G.J. Clarkson, and M. Wills J. Am. Chem. Soc. 2004 986
57. J.L. Namy, J. Souppe, J. Collin, and H.B. Kagan J. Org. Chem. 1984 2045
58. G. Zassinovich, G. Mestroni, and S. Glidiali Chem. Rev. 1992 1051
59. M. Yiǧit, B. Yiǧit, I. Özdemir, E. Çetinkaya, and B. Çetinkaya Appl. Organomet. Chem. 2006 322
60. J.W. Faller, and A.R. Lavoie Organometallics 20 2001 5245
61. I. Özdemir, and S. Yaşar Trans. Met. Chem. 30 2005 831
62. M.A. Bennet, and A.K. Smith J. Chem. Soc. Dalton Trans. 1974 233