Mechanism of the asymmetric hydrogenation of exocyclic α,β- unsaturated carbonyl compounds with an iridium/BiphPhox catalyst: NMR and DFT studies

Angewandte Chemie - International Edition

Volumn 53, Issue 7, 2014, Pages 1901-1905

  Liu, Yuanyuan ^a   Gridnev, Ilya D ^b   Zhang, Wanbin ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

density functional calculations; hydrogenation; iridium; NMR spectroscopy; reaction mechanisms

Indexed keywords

ASYMMETRIC HYDROGENATION; COMPUTATIONAL ANALYSIS; DINUCLEAR IRIDIUMS; ENANTIOSELECTION; EXPERIMENTAL VALUES; INTRA-MOLECULAR HYDROGEN BONDS; REACTION MECHANISM; UNSATURATED CARBONYL COMPOUNDS;

CARBONYL COMPOUNDS; CATALYSTS; DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; IRIDIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROGENATION;

EID: 84893606204     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309677     Document Type: Article

References (94)

1. Y. Zhu, K. Burgess, Acc. Chem. Res. 2012, 45, 1623
2. D.-S. Wang, Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 2012, 112, 2557
3. A. Cadu, P. G. Andersson, J. Organomet. Chem. 2012, 714, 3
4. J.-H. Xie, Q.-L. Zhou, Acta Chim. Sin. 2012, 70, 1427
5. J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713
6. S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402
7. T. Ikariya, A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300
8. N. B. Johnson, I. C. Lennon, P. H. Moran, J. A. Ramsden, Acc. Chem. Res. 2007, 40, 1291
9. A. J. Minnaard, B. L. Feringa, L. Lefort, J. G. de Vries, Acc. Chem. Res. 2007, 40, 1267
10. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029.
11. C. Liu, J.-H. Xie, Y.-L. Li, J.-Q. Chen, Q.-L. Zhou, Angew. Chem. 2013, 125, 621
12. Angew. Chem. Int. Ed. 2013, 52, 593
13. Y. Li, K. Dong, Z. Wang, K. Ding, Angew. Chem. 2013, 125, 6880
14. Angew. Chem. Int. Ed. 2013, 52, 6748
15. K. Dong, Z. Wang, K. Ding, J. Am. Chem. Soc. 2012, 134, 12474
16. T. Touge, T. Hakamata, H. Nara, T. Kobayashi, N. Sayo, T. Saito, Y. Kayaki, T. Ikariya, J. Am. Chem. Soc. 2011, 133, 14960
17. M. Ito, C. Kobayashi, A. Himizu, T. Ikariya, J. Am. Chem. Soc. 2010, 132, 11414
18. G. Hou, W. Li, M. Ma, X. Zhang, X. Zhang, J. Am. Chem. Soc. 2010, 132, 12844
19. K. Tamura, M. Sugiya, K. Yoshida, A. Yanagisawa, T. Imamoto, Org. Lett. 2010, 12, 4400.
20. D. H. Woodmansee, A. Pfaltz, Chem. Commun. 2011, 47, 7912
21. D. Woodmansee, A. Pfaltz, Top. Organomet. Chem. 2011, 34, 31
22. K. Källström, I. Munslow, P. G. Andersson, Chem. Eur. J. 2006, 12, 3194; For selected recent examples, see
23. P.-C. Yan, G.-L. Zhu, J.-H. Xie, X.-D. Zhang, Q.-L. Zhou, Y.-Q. Li, W.-H. Shen, D.-Q. Che, Org. Process Res. Dev. 2013, 17, 307
24. T. Zhou, B. Peters, M. F. Maldonado, T. Govender, P. G. Andersson, J. Am. Chem. Soc. 2012, 134, 13592
25. S.-F. Zhu, Y.-B. Yu, S. Li, L.-X. Wang, Q.-L. Zhou, Angew. Chem. 2012, 124, 9002
26. Angew. Chem. Int. Ed. 2012, 51, 8872
27. X. Wang, Z. Han, Z. Wang, K. Ding, Angew. Chem. 2012, 124, 960
28. Angew. Chem. Int. Ed. 2012, 51, 936
29. J.-H. Xie, X.-Y. Liu, X.-H. Yang, J.-B. Xie, L.-X. Wang, Q.-L. Zhou, Angew. Chem. 2012, 124, 205
30. Angew. Chem. Int. Ed. 2012, 51, 201
31. D. H. Woodmansee, M.-A. Müller, L. Tröndlin, E. Hörmann, A. Pfaltz, Chem. Eur. J. 2012, 18, 13780
32. A. Ganic̈, A. Pfaltz, Chem. Eur. J. 2012, 18, 6724
33. J. J. Verendel, T. Zhou, J.-Q. Li, A. Paptchikhine, O. Lebedev, P. G. Andersson, J. Am. Chem. Soc. 2010, 132, 8880
34. Y. Zhang, Z. Han, F. Li, K. Ding, A. Zhang, Chem. Commun. 2010, 46, 156
35. Z. Han, Z. Wang, X. Zhang, K. Ding, Angew. Chem. 2009, 121, 5449
36. Angew. Chem. Int. Ed. 2009, 48, 5345
37. P. Cheruku, A. Paptchikhine, T. L. Church, P. G. Andersson, J. Am. Chem. Soc. 2009, 131, 8285
38. S. Li, S.-F. Zhu, C.-M. Zhang, S. Song, Q.-L. Zhou, J. Am. Chem. Soc. 2008, 130, 8584
39. W. Lu, Y. Chen, X. Hou, Angew. Chem. 2008, 120, 10287
40. Angew. Chem. Int. Ed. 2008, 47, 10133
41. S.-M. Lu, C. Bolm, Angew. Chem. 2008, 120, 9052
42. Angew. Chem. Int. Ed. 2008, 47, 8920.
43. A. Schumacher, M. Bernasconi, A. Pfaltz, Angew. Chem. 2013, 125, 7570
44. Angew. Chem. Int. Ed. 2013, 52, 7422
45. Z.-S. Ye, R.-N. Guo, X.-F. Cai, M.-W. Chen, L. Shi, Y.-G. Zhou, Angew. Chem. 2013, 125, 3773
46. Angew. Chem. Int. Ed. 2013, 52, 3685
47. D. Rageot, D. H. Woodmansee, B. Pugin, A. Pfaltz, Angew. Chem. 2011, 123, 9772
48. Angew. Chem. Int. Ed. 2011, 50, 9598
49. Y. Zhu, Y. Fan, K. Burgess, J. Am. Chem. Soc. 2010, 132, 6249
50. G.-H. Hou, J.-H. Xie, P.-C. Yan, Q.-L. Zhou, J. Am. Chem. Soc. 2009, 131, 1366
51. M. C. Perry, X. Cui, M. T. Powell, D.-R. Hou, J. H. Reibenspies, K. Burgess, J. Am. Chem. Soc. 2003, 125, 113
52. D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533
53. Angew. Chem. Int. Ed. 2001, 40, 3425.
54. S. Gruber, M. Neuburger, A. Pfaltz, Organometallics 2013, 32, 4702
55. J. Mazuela, P.-O. Norrby, P. G. Andersson, O. Pàmies, M. Diéguez, J. Am. Chem. Soc. 2011, 133, 13634
56. K. H. Hopmann, A. Bayer, Organometallics 2011, 30, 2483
57. S. Li, S.-F. Zhu, J.-H. Xie, S. Song, C.-M. Zhang, Q.-L. Zhou, J. Am. Chem. Soc. 2010, 132, 1172
58. T. L. Church, T. Rasmussen, P. G. Andersson, Organometallics 2010, 29, 6769
59. X. Cui, Y. Fan, M. B. Hall, K. Burgess, Chem. Eur. J. 2005, 11, 6859
60. C. Mazet, S. P. Smidt, M. Meuwly, A. Pfaltz, J. Am. Chem. Soc. 2004, 126, 14176
61. Y. Fan, X. Cui, K. Burgess, M. B. Hall, J. Am. Chem. Soc. 2004, 126, 16688
62. R. Dietiker, P. Chen, Angew. Chem. 2004, 116, 5629
63. Angew. Chem. Int. Ed. 2004, 43, 5513
64. P. Brandt, C. Hedberg, P. G. Andersson, Chem. Eur. J. 2003, 9, 339
65. R. H. Crabtree, R. J. Uriarte, Inorg. Chem. 1983, 22, 4152
66. R. H. Crabtree, P. C. Demou, D. Eden, J. M. Mihelic, C. A. Parnell, J. M. Quirk, G. E. Morris, J. Am. Chem. Soc. 1982, 104, 6994.
67. P. A. Dub, T. Ikariya, J. Am. Chem. Soc. 2013, 135, 2604
68. J. I. Václavík, M. Kuzma, J. Přech, P. Kačer, Organometallics 2011, 30, 4822
69. J. W. Handgraaf, J. N. H. Reek, E. J. Meijer, Organometallics 2003, 22, 3150
70. C. P. Casey, J. B. Johnson, J. Org. Chem. 2003, 68, 1998
71. M. Yamakawa, I. Yamada, R. Noyori, Angew. Chem. 2001, 113, 2900
72. Angew. Chem. Int. Ed. 2001, 40, 2818
73. D. G. I. Petra, J. N. H. Reek, J.-W. Handgraaf, E. J. Meijer, P. Dierkes, P. C. J. Kamer, J. Brussee, H. E. Schoemaker, L. P. W. N. M. Van, Chem. Eur. J. 2000, 6, 2818
74. D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580
75. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297
76. Angew. Chem. Int. Ed. Engl. 1997, 36, 285.
77. I. D. Gridnev, T. Imamoto, Chem. Commun. 2009, 7447
78. J. M. Brown, in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999, pp. 119-182. For selected examples, see
79. T. Imamoto, K. Tamura, Z. Zhang, Y. Horiuchi, M. Sugiya, K. Yoshida, A. Yanagisawa, I. D. Gridnev, J. Am. Chem. Soc. 2012, 134, 1754
80. I. D. Gridnev, T. Imamoto, G. Hoge, M. Kouchi, H. Takahashi, J. Am. Chem. Soc. 2008, 130, 2560
81. I. D. Gridnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 2000, 122, 7183
82. A. S. C. Chan, J. Halpern, J. Am. Chem. Soc. 1980, 102, 838
83. J. M. Brown, P. A. Chaloner, J. Chem. Soc. Chem. Commun. 1978, 321
84. R. R. Schrock, J. A. Osborn, J. Am. Chem. Soc. 1976, 98, 2134.
85. Y. Liu, W. Zhang, Angew. Chem. 2013, 125, 2259
86. Angew. Chem. Int. Ed. 2013, 52, 2203
87. Y. Liu, D. Yao, K. Li, F. Tian, F. Xie, W. Zhang, Tetrahedron 2011, 67, 8445
88. Y. Liu, G. Yang, D. Yao, F. Tian, W. Zhang, Sci. China Chem. 2011, 54, 87
89. F. Tian, D. Yao, Y. Liu, W. Zhang, Adv. Synth. Catal. 2010, 352, 1841.
90. C. Kohrt, W. Baumann, A. Spannenberg, H.-J. Drexler, I. D. Gridnev, D. Heller, Chem. Eur. J. 2013, 19, 7443
91. C. Kohrt, G. Wienhöfer, C. Pribbenow, M. Beller, D. Heller, ChemCatChem 2013, 5, 2818.
92. P. B. Crowley, M. Ubbink, Acc. Chem. Res. 2003, 36, 723
93. S. Scanu, J. M. Foerster, G. M. Ullmann, M. Ubbink, J. Am. Chem. Soc. 2013, 135, 7681.
94. A. Hamza, G. Schubert, T. Soõs, I. Pápai, J. Am. Chem. Soc. 2006, 128, 13151.