Efficient Ru(II)-catalyzed asymmetric hydrogenation of simple ketones with C 2-symmetric planar chiral metallocenyl phosphinooxazoline ligands

Tetrahedron

Volumn 68, Issue 16, 2012, Pages 3295-3299

  Guo, Hui ^a   Liu, Delong ^a   Butt, Nicholas A ^a   Liu, Yangang ^a   Zhang, Wanbin ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Ketone; Phosphinooxazoline ligands; Planar chirality; Ru catalyzed asymmetric hydrogenation

Indexed keywords

ACETOPHENONE; HYDROGEN; KETONE DERIVATIVE; LIGAND; OXAZOLINE DERIVATIVE; RUTHENIUM; SOLVENT;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 84862777376     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.075     Document Type: Article

References (61)

1. R. Noyori Angew. Chem., Int. Ed. 41 2002 2008 2022
2. W.S. Knolwes Adv. Synth. Catal. 345 2003 3 13
3. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029 3069
4. G. Desimoni, G. Faita, and K.A. Jørgensen Chem. Rev. 106 2006 3561 3651
5. W. Zhang, Y. Chi, and X. Zhang Acc. Chem. Res. 40 2007 1278 1290
6. J.-H. Xie, S.-F. Zhu, and Q.-L. Zhou Chem. Rev. 111 2010 1713 1760
7. T. Hayashi, and A. Togni Ferrocenes 1995 VCH Weinheim, Germany
8. A. Togni, and R. Haltermann Metallocenes 1998 VCH Weinheim, Germany
9. H. Blaser, F. Spindler, E. Jacobsen, A. Pfaltz, and H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 3 1999 Springer Berlin 1427
10. L.-X. Dai, T. Tu, S.-L. You, W.-P. Deng, and X.-L. Hou Acc. Chem. Res. 36 2003 659 667
11. T.J. Colacot Chem. Rev. 103 2003 3101 3118
12. S.-I. Fukuzawa, D. Wachi, T. Suzuki, and S. Itoh J. Org. Chem. 69 2004 4991 4996
13. X.-L. Hou, and N. Sun Org. Lett. 6 2004 4399 4401
14. A. Moyano, M. Rosol, R.M. Moreno, C. Lopez, and M.A. Maestro Angew. Chem., Int. Ed. 44 2005 1865 1869
15. S. Ozcubukcu, F. Schmidt, and C. Bolm Org. Lett. 7 2005 1407 1409
16. R.G. Arrayas, J. Adrio, and J.C. Carretero Angew. Chem., Int. Ed. 45 2006 7674 7715
17. W. Chen, W. Mbafor, S.M. Roberts, and J. Whittall J. Am. Chem. Soc. 128 2006 3922 3923
18. B. Jiang, and Z.-G. Huang Tetrahedron Lett. 48 2007 1703 1706
19. A.E. Ashley, R.T. Cooper, G.G. Wildgoose, J.C. Green, and D. O'Hare J. Am. Chem. Soc. 130 2008 15662 15677
20. K. Zhang, Q. Peng, X.-L. Hou, and Y.-D. Wu Angew. Chem., Int. Ed. 47 2008 1741 1744
21. R. Sebesta, and F. Bilcik Tetrahedron: Asymmetry 20 2009 1892 1896
22. B. Hu, M. Meng, Z. Wang, W. Du, J.S. Fossey, X. Hu, and W.-P. Deng J. Am. Chem. Soc. 132 2010 17041 17044
23. J. Niemeyer, J. Cloppenburg, R. Frohlich, G. Kehr, and G. Erker J. Organomet. Chem. 695 2010 1801 1812
24. S. Madhavan, and P. Shanmugam Org. Lett. 13 2011 1590 1593
25. G. Hua, D. Liu, F. Xie, and W. Zhang Tetrahedron Lett. 48 2007 385 388
26. D. Liu, F. Xie, and W. Zhang Tetrahedron Lett. 48 2007 585 588
27. D. Liu, F. Xie, and W. Zhang Tetrahedron Lett. 48 2007 7591 7594
28. D. Liu, F. Xie, and W. Zhang J. Org. Chem. 72 2007 6992 6997
29. D. Liu, F. Xie, X. Zhao, and W. Zhang Tetrahedron 64 2008 3561 3566
30. F. Xie, D. Liu, and W. Zhang Tetrahedron Lett. 49 2008 1012 1015
31. Y. Wang, D. Liu, Q. Meng, and W. Zhang Tetrahedron: Asymmetry 20 2009 2510 2512
32. X. Zhao, D. Liu, F. Xie, and W. Zhang Tetrahedron 65 2009 512 517
33. W. Zhang, and D. Liu L.-X. Dai, X.-L. Hou, Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications Vol. 14 2010 VCH Weinheim, Germany 175 214
34. X. Zhao, D. Liu, F. Xie, Y. Liu, and W. Zhang Org. Biomol. Chem. 9 2011 1871 1875
35. K. Abdur-Rashid, M. Faatz, A.J. Lough, and R.H. Morris J. Am. Chem. Soc. 123 2001 7473 7474
36. R. Noyori, and T. Ohkuma Angew. Chem., Int. Ed. 40 2001 40 73
37. K. Aikawa, and K. Mikami Angew. Chem., Int. Ed. 42 2003 5455 5458
38. J.-P. Genet Acc. Chem. Res. 36 2003 908 918
39. D.G. Genov, and D.J. Ager Angew. Chem., Int. Ed. 43 2004 2816 2819
40. H. Huang, T. Okuno, K. Tsuda, M. Yoshimura, and M. Kitamura J. Am. Chem. Soc. 128 2006 8716 8717
41. F. Naud, C. Malan, F. Spindler, C. Rüggeberg, A. Schmidt, and H.U. Blaser Adv. Synth. Catal. 348 2006 47 50
42. W.P. Hems, M. Groarke, A. Zanotti-Gerosa, and G.A. Grasa Acc. Chem. Res. 40 2007 1340 1347
43. M. Ito, and T. Ikariya Chem. Commun. 2007 5134 5142
44. W. Li, X. Sun, L. Zhou, G. Hou, S. Yu, and X. Zhang J. Org. Chem. 74 2008 1397 1399
45. H. Ooka, N. Arai, K. Azuma, N. Kurono, and T. Ohkuma J. Org. Chem. 73 2008 9084 9093
46. Q. Zhu, D. Shi, C. Xia, and H. Huang Chem.-Eur. J. 17 2011 7760 7763
47. N. Arai, M. Akashi, S. Sugizaki, H. Ooka, T. Inoue, and T. Ohkuma Org. Lett. 12 2010 3380 3383
48. B. Stegink, L. van Boxtel, L. Lefort, A.J. Minnaard, B.L. Feringa, and J.G. de Vries Adv. Synth. Catal. 352 2010 2621 2628
49. W. Zhang, Y. Adachi, T. Hirao, and I. Ikeda Tetrahedron: Asymmetry 7 1996 451 460
50. W. Zhang, T. Hirao, and I. Ikeda Tetrahedron Lett. 37 1996 4545 4548
51. W. Zhang, T. Kida, Y. Nakatsuji, and I. Ikeda Tetrahedron Lett. 37 1996 7995 7998
52. W. Zhang, T. Shimanuki, T. Kida, Y. Nakatsuji, and I. Ikeda J. Org. Chem. 64 1999 6247 6251
53. M. Palmer, T. Walsgrove, and M. Wills J. Org. Chem. 62 1997 5226 5228
54. W. Ye, M. Zhao, W. Du, Q. Jiang, K. Wu, P. Wu, and Z. Yu Chem. - Eur. J. 17 2011 4737 4741
55. H.L. Ngo, and W. Lin J. Org. Chem. 70 2005 1177 1187
56. D.-M. Du, T. Fang, J. Xu, and S.W. Zhang Org. Lett. 8 2006 1327 1330
57. B. Martín-Matute, M. Edin, K. Bogár, F.B. Kaynak, and J.-E. Bäckvall J. Am. Chem. Soc. 127 2005 8817 8825
58. Y. Li, Y. Zhou, Q. Shi, K. Ding, R. Noyori, and C.A. Sandoval Adv. Synth. Catal. 353 2011 495 500
59. M.J. Burk, W. Hems, D. Herzberg, C. Malan, and A. Zanotti-Gerosa Org. Lett. 2 2000 4173 4176
60. D.A. Evans, F.E. Michael, J.S. Tedrow, and K.R. Campos J. Am. Chem. Soc. 125 2003 3534 3543
61. M. Kallergi, D. Kalaitzakis, and I. Smonou Eur. J. Org. Chem. 2011 3946 3950