Palladium-catalyzed asymmetric hydrogenation of fluorinated quinazolinones

Tetrahedron Letters

Volumn 54, Issue 46, 2013, Pages 6161-6163

  Duan, Ying ^b   Zhu, Xiao Yan ^a   Ma, Jun An ^a   Zhou, Yong Gui ^b  

^a TIANJIN UNIVERSITY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Asymmetric hydrogenation; Fluorinated imines; Palladium; Quinazolinones

Indexed keywords

FLUORINE DERIVATIVE; PALLADIUM; PHOSPHATE; QUINAZOLINONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS;

EID: 84885477099     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.08.078     Document Type: Article

References (69)

1. J.W. Corbett, S.S. Ko, J.D. Rodgers, L.A. Gearhart, N.A. Magnus, L.T. Bacheler, S. Diamond, S. Jeffrey, R.M. Klabe, B.C. Cordova, S. Garber, K. Logue, G.L. Trainor, P.S. Anderson, and S.K. Erickson-Viitanen J. Med. Chem. 43 2000 2019
2. Kresge, K.; Big Leaks in the Bristol Pipeline, The Amfar Treatment Insider 2003, 4, No. 5.
3. C. Hoffmann, J.K. Rockstroh, and B.S. Kamps HIV Medicine 2007 2007 Flying Publisher Paris
4. H. Hasegawa, M. Muraoka, K. Matsui, and A. Kojima Bioorg. Med. Chem. Lett. 13 2003 3471
5. J.-A. Ma, and D. Cahard J. Fluorine Chem. 128 2007 975
6. D. O'Hagan Chem. Soc. Rev. 37 2008 308
7. N. Shibata, S. Mizuta, and H. Kawai Tetrahedron: Asymmetry 19 2008 2633
8. J.-A. Ma, and D. Cahard Chem. Rev. 108 2008 PR1
9. J. Nie, H.-C. Guo, D. Cahard, and J.-A. Ma Chem. Rev. 111 2011 455
10. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475
11. T. Besset, C. Schneider, and D. Cahard Angew. Chem., Int. Ed. 51 2012 5048
12. For enantisoselective transformations of the fluorinated quinazolinones, see: M.A. Huffman, N. Yasuda, A.E. DeCamp, and E.J.J. Grabowski J. Org. Chem. 60 1995 1590
13. G.S. Kauffman, G.D. Harris, R.L. Dorow, B.R.P. Stone, R.L. Parsons, J.A. Pesti, N.A. Magnus, J.M. Fortunak, P.N. Confalone, and W.A. Nugent Org. Lett. 2 2000 3119
14. N.A. Magnus, P.N. Confalone, and L. Storace Tetrahedron Lett. 41 2000 3015
15. N.A. Magnus, P.N. Confalone, L. Storace, M. Patel, C.C. Wood, W.P. Davis, and R.L. Parsons J. Org. Chem. 68 2003 754
16. B. Jiang, and Y.G. Si Angew. Chem., Int. Ed. 43 2004 216
17. B. Jiang, J.J. Dong, Y.G. Si, X.L. Zhao, Z.G. Huang, and M. Xu Adv. Synth. Catal. 350 2008 1360
18. H. Xie, Y. Zhang, S. Zhang, X. Chen, and W. Wang Angew. Chem., Int. Ed. 50 2011 11773
19. F.-G. Zhang, H. Ma, J. Nie, Y. Zheng, Q. Gao, and J.-A. Ma Adv. Synth. Catal. 354 2012 1422
20. F.-G. Zhang, X.-Y. Zhu, S. Li, J. Nie, and J.-A. Ma Chem. Commun. 2012 11552
21. H. Xie, A. Song, X. Zhang, X. Chen, H. Li, C. Sheng, and W. Wang Chem. Commun. 2013 928
22. H.-N. Yuan, S. Wang, J. Nie, W. Meng, Q. Yao, and J.-A. Ma Angew. Chem., Int. Ed. 52 2013 3869
23. For review of asymmetric hydrogenation of imines, see: J.-H. Xie, S.-F. Zhu, and Q.-L. Zhou Chem. Rev. 111 2011 1713
24. For recent review of Pd-catalyzed asymmetric hydrogenation, see: Q.-A. Chen, Z.-S. Ye, Y. Duan, and Y.-G. Zhou Chem. Soc. Rev. 42 2013 497
25. D. Drago, and P.S. Pregosin Organometallics 21 2002 1208
26. M.D. Jones, R. Raja, J.M. Thomas, B.F.G. Johnson, D.W. Lewis, J. Rouzaud, and K.D.M. Harris Angew. Chem., Int. Ed. 42 2003 4326
27. Y. Tsuchiya, Y. Hamashima, and M. Sodeoka Org. Lett. 8 2006 4851
28. D. Monguchi, C. Beemelmanns, D. Hashizume, Y. Hamashima, and M. Sodeoka J. Organomet. Chem. 693 2008 867
29. A. Arnanz, C. González-Arellano, A. Juan, G. Villaverde, A. Corma, M. Iglesias, and F. Sánchez Chem. Commun. 2010 3001
30. M. Boronat, A. Corma, C. González-Arellano, M. Iglesias, and F. Sánchez Organometallics 29 2010 134
31. D.-S. Wang, D.-W. Wang, and Y.-G. Zhou Synlett 2011 947
32. R. Raja, J.M. Thomas, M.D. Jones, B.F.G. Johnson, and D.E.W. Vaughan J. Am. Chem. Soc. 125 2003 14982
33. Y.-Q. Wang, S.-M. Lu, and Y.-G. Zhou Org. Lett. 7 2005 3235
34. N.S. Goulioukina, G.N. Bondarenko, A.V. Bogdanov, K.N. Gavrilov, and I.P. Beletskaya Eur. J. Org. Chem. 2009 510
35. C.Q. Wang, G.Q. Yang, J. Zhuang, and W.B. Zhang Tetrahedron Lett. 51 2010 2044
36. B. Teng, J. Zheng, H. Huang, and P. Huang Chin. J. Chem. 29 2011 1312
37. X.-Y. Zhou, D.-S. Wang, M. Bao, and Y.-G. Zhou Tetrahedron Lett. 52 2011 2826
38. A. Suzuki, M. Mae, H. Amii, and K. Uneyama J. Org. Chem. 69 2004 5132
39. Y.-Q. Wang, and Y.-G. Zhou Synlett 2006 1189
40. Q. Yang, G. Shang, W. Gao, J. Deng, and X. Zhang Angew. Chem., Int. Ed. 45 2006 3832
41. Y.-Q. Wang, S.-M. Lu, and Y.-G. Zhou J. Org. Chem. 72 2007 3729
42. Y.-Q. Wang, C.-B. Yu, D.-W. Wang, X.-B. Wang, and Y.-G. Zhou Org. Lett. 10 2008 2071
43. C.-B. Yu, D.-W. Wang, and Y.-G. Zhou J. Org. Chem. 74 2009 5633
44. X.-Y. Zhou, M. Bao, and Y.-G. Zhou Adv. Synth. Catal. 353 2011 84
45. N.S. Goulioukina, I.A. Shergold, G.N. Bondarenko, M.M. Ilyin, V.A. Davankov, and I.P. Beletskaya Adv. Synth. Catal. 354 2012 2727
46. C.-B. Yu, K. Gao, D.-S. Wang, L. Shi, and Y.-G. Zhou Chem. Commun. 2011 5052
47. C.-B. Yu, K. Gao, Q.-A. Chen, M.-W. Chen, and Y.-G. Zhou Tetrahedron Lett. 53 2012 2560
48. D.-S. Wang, Q.-A. Chen, W. Li, C.-B. Yu, Y.-G. Zhou, and X. Zhang J. Am. Chem. Soc. 132 2010 8909
49. Y. Duan, M.-W. Chen, Z.-S. Ye, D.-S. Wang, Q.-A. Chen, and Y.-G. Zhou Chem. Eur. J. 17 2011 7193
50. D.-S. Wang, J. Tang, Y.-G. Zhou, M.-W. Chen, C.-B. Yu, Y. Duan, and G.-F. Jiang Chem. Sci. 2 2011 803
51. D.-S. Wang, Z.-S. Ye, Q.-A. Chen, Y.-G. Zhou, C.-B. Yu, H.-J. Fan, and Y. Duan J. Am. Chem. Soc. 133 2011 8866
52. Y. Duan, M.-W. Chen, Q.-A. Chen, C.-B. Yu, and Y.-G. Zhou Org. Biomol. Chem. 10 2012 1235
53. D.-S. Wang, Q.-A. Chen, S.-M. Lu, and Y.-G. Zhou Chem. Rev. 112 2012 2557
54. H. Abe, H. Amii, and K. Uneyama Org. Lett. 3 2001 313
55. M.-W. Chen, Y. Duan, Q.-A. Chen, D.-S. Wang, C.-B. Yu, and Y.-G. Zhou Org. Lett. 12 2010 5075
56. J.-A. Ma, and D. Cahard J. Org. Chem. 68 2003 8726
57. J.A. Ma, and D. Cahard Chem. Rev. 104 2004 6119
58. J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, and J.-A. Ma Org. Lett. 9 2007 3053
59. H.-F. Cui, K.-Y. Dong, G.-W. Zhang, L. Wang, and J.-A. Ma Chem. Commun. 2007 2284
60. G.-W. Zhang, L. Wang, J. Nie, and J.-A. Ma Adv. Synth. Catal. 350 2008 1457
61. J. Nie, G.-W. Zhang, L. Wang, A. Fu, Y. Zheng, and J.-A. Ma Chem. Commun. 2009 2356
62. J. Nie, G.-W. Zhang, L. Wang, D.-H. Zheng, Y. Zheng, and J.-A. Ma Eur. J. Org. Chem. 2009 3145
63. T. Wang, G.-W. Zhang, Y. Teng, J. Nie, Y. Zheng, and J.-A. Ma Adv. Synth. Catal. 352 2010 2773
64. Y. Zheng, and J.-A. Ma Adv. Synth. Catal. 352 2010 2745
65. L. Wang, W. Meng, C.-L. Zhu, Y. Zhen, J. Nie, and J.-A. Ma Angew. Chem., Int. Ed. 50 2011 9442
66. G.-W. Zhang, W. Meng, H. Ma, J. Nie, W.-Q. Zhang, and J.-A. Ma Angew. Chem., Int. Ed. 50 2011 3538
67. J. Nie, X.-J. Li, D.-H. Zheng, F.-G. Zhang, S. Cui, and J.-A. Ma J. Fluorine Chem. 132 2011 468
68. F. Li, J. Nie, J.-W. Wu, Y. Zheng, and J.-A. Ma J. Org. Chem. 77 2012 2398
69. For the preparation of Pd-catalyst complex, see Supplementary data and P.J. Stang, B. Olenyuk, and A.M. Arif Organometallics 14 1995 5281