Asymmetric hydrogenation of aromatic ketones using an iridium(I) catalyst containing ferrocene-based P-N-N tridentate ligands

Tetrahedron Asymmetry

Volumn 24, Issue 24, 2013, Pages 1567-1571

  Nie, Huifang ^a   Zhou, Gang ^a   Wang, Quanjun ^a   Chen, Weiping ^a   Zhang, Shengyong ^a  

^a FOURTH MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; FERROCENE DERIVATIVE; IRIDIUM; IRIDIUM COMPLEX; KETONE; LIGAND; PHENYL GROUP; PYRIDINE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84890107618     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.10.012     Document Type: Article

References (49)

1. For reviews, see: R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 Wiley New York
2. E.N. Jacobsen, A. Pfaltz, and H. Yamamoto Comprehensive Asymmetric Catalysis Vols 1-3 1999 Springer Berlin
3. I. Ojima Catalytic Asymmetric Synthesis 2nd ed. 2000 Wiley-Blackwell New York
4. G.-Q. Lin, Y.-M. Li, and A.S.C. Chan Principles and Applications of Asymmetric Synthesis 2001 Wiley-Blackwell New York
5. H. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103
6. I.C. Lennon, and P.H. Moran Curr. Opin. Drug Discovery Dev. 6 2003 855
7. C.J. Elsevier, and J.N.H. De Vries The Comprehensive Handbook of Homogeneous Hydrogenation 2006 Wiley-VCH Weinheim
8. For reviews, see: M. Kitamura, and R. Noyori S.-I. Murahashi, Ruthenium in Organic Synthesis 2004 Wiley-VCH Weinheim Chapter 2
9. R. Noyori, and T. Ohkuma Angew. Chem., Int. Ed. 40 2001 40 For a leading example
10. T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 117 1995 2675
11. T. Ohkuma, H. Ooka, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 117 1995 10417
12. H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A.F. England, T. Ikariya, and R. Noyori Angew. Chem., Int. Ed. 37 1998 1703
13. T. Ohkuma, M. Koizumi, H. Doucet, T. Pharm, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 120 1998 13529
14. For the mechanism of the asymmetric hydrogenation of ketones catalyzed by the Noyori catalyst, see: M. Yamakawa, H. Ito, and R. Noyori J. Am. Chem. Soc. 122 2000 1466
15. R. Noyori, M. Yamakawa, and S. Hashiguchi J. Org. Chem. 66 2001 7931
16. R. Hartmann, and P. Chan Angew. Chem., Int. Ed. 40 2001 3581
17. K. Abdur-Rashid, M. Faatz, A.J. Lough, and R.H. Morris J. Am. Chem. Soc. 123 2001 7473
18. C.A. Sandoval, T. Ohkuma, K. Muniz, and R. Noyori J. Am. Chem. Soc. 125 2003 13490
19. S.E. Clapham, A. Hadzovic, and R.H. Morris Coord. Chem. Rev. 248 2004 2201
20. R.J. Hamilton, C.G. Leong, G. Bigam, M. Miskolzie, and S.H. Bergens J. Am. Chem. Soc. 127 2005 4152
21. W.P. Hems, M. Groarke, A. Zanotti-Gerosa, and G.A. Grasa Acc. Chem. Res. 40 2007 1340
22. C.A. Sandoval, Y. Li, K. Ding, and R. Noyori Chem. Asian J. 3 2008 1801
23. For selected examples using chiral phosphines other than BINAP as ligands, see: P. Cao, and X. Zhang J. Org. Chem. 64 1999 2127
24. M.J. Burk, W. Hems, D. Herzberg, C. Malan, and A. Zanotti-Gerosa Org. Lett. 2 2000 4173
25. J.-H. Xie, L.-X. Wang, Y. Fu, S.-F. Zhu, B.-M. Fan, H.-F. Duan, and Q.-L. Zhou J. Am. Chem. Soc. 125 2003 4404
26. J. Wu, J.-X. Ji, R. Guo, C.-H. Yeung, and A.S.C. Chan Chem. Eur. J. 9 2003 2963
27. J.P. Henschke, A. Zanotti-Gerosa, P. Moran, P. Harrison, B. Mullen, G. Casy, and I.C. Lennon Tetrahedron Lett. 44 2003 4379
28. A. Hu, H.L. Ngo, and W. Lin Org. Lett. 6 2004 2937
29. D.G. Genov, and D.J. Ager Angew. Chem., Int. Ed. 43 2004 2816
30. R. Guo, R.H. Morris, and D. Song J. Am. Chem. Soc. 127 2005 516
31. J.-H. Xie, Z.-T. Zhou, W.-L. Kong, and Q.-L. Zhou J. Am. Chem. Soc. 129 2007 1868
32. W. Li, X. Sun, L. Zhou, G. Hou, S. Yu, and X. Zhang J. Org. Chem. 74 2009 1397 for using racemic BINAP or chirally flexible diphosphine ligands
33. T. Ohkuma, H. Doucet, T. Pham, K. Mikami, T. Korenaga, M. Terada, and R. Noyori J. Am. Chem. Soc. 120 1998 1086
34. K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, and R. Noyori Angew. Chem., Int. Ed. 38 1999 495
35. K. Mikami, T. Korenaga, T. Ohkuma, and R. Noyori Angew. Chem., Int. Ed. 39 2000 3707
36. K. Mikami, K. Wakabayashi, and K. Aikawa Org. Lett. 8 2006 1517
37. Q. Jing, C.A. Sandoval, Z. Wang, and K. Ding Eur. J. Org. Chem. 2006 3606 For a bulky achiral monophosphine as a ligand, see
38. Q. Jing, X. Zhang, J. Sun, and K. Ding Adv. Synth. Catal. 347 2005 1193
39. 2(diamine)] type catalysts, chiral ruthenacyclic catalysts have recently been utilized in the highly active and enantioselective hydrogenation of ketones, see: K. Matsumura, N. Arai, K. Hori, T. Saito, N. Sayo, and T. Ohkuma J. Am. Chem. Soc. 133 2011 10696
40. W. Baratta, G. Chelucci, S. Magnolia, K. Siega, and P. Rigo Chem. Eur. J. 15 2009 726
41. J.-H. Xie, X.-Y. Liu, J.-B. Xie, L.-X. Wang, and Q.-L. Zhou Angew. Chem., Int. Ed. 50 2011 7329
42. J.-B. Xie, J.-H. Xie, X.-Y. Liu, Q.-Q. Zhang, and Q.-L. Zhou Chem. Asian J. 6 2011 899
43. W. Chen, W. Mbafor, S.M. Roberts, and J. Whittall Tetrahedron: Asymmetry 17 2006 1161
44. W. Chen, W. Mbafor, S.M. Roberts, and J. Whittall J. Am. Chem. Soc. 128 2006 3922
45. W. Chen, S.M. Roberts, J. Whittall, and A. Steiner Chem. Commun. 2006 2916
46. W. Chen, P.J. McCormack, K. Mohammed, W. Mbafor, S.M. Roberts, and J. Whittall Angew. Chem., Int. Ed. 46 2007 4141
47. W. Chen, F. Spindler, B. Pugin, and U. Nettekoven Angew. Chem., Int. Ed. 52 2013 8652
48. J.E.D. Martins, and M. Wills Tetrahedron 65 2009 5782
49. T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto, and M. Kumada Bull. Chem. Soc. Jpn. 53 1980 1138