Enantioselective synthesis of amines: General, efficient iron-catalyzed asymmetric transfer hydrogenation of imines

Angewandte Chemie - International Edition

Volumn 49, Issue 44, 2010, Pages 8121-8125

  Zhou, Shaolin ^a   Fleischer, Steffen ^a   Junge, Kathrin ^a   Das, Shoubhik ^a   Addis, Daniele ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Asymmetric catalysis; Enantioselectivity; Imines; Iron catalysis; Transfer hydrogenation

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC TRANSFER HYDROGENATION; BROAD APPLICATION; CATALYTIC TRANSFER HYDROGENATION; CHIRAL AMINES; ENANTIOSELECTIVE SYNTHESIS; HIGH YIELD; IMINES; IRON AGE; IRON CATALYSIS; IRON CATALYST; TRANSFER HYDROGENATIONS;

AMINES; CATALYSTS; ENANTIOSELECTIVITY; HYDROGENATION;

CATALYSIS;

AMINE; HYDROGEN; IMINE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

AMINES; CATALYSIS; HYDROGEN; IMINES; STEREOISOMERISM;

EID: 78249265971     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002456     Document Type: Article

References (119)

1. For reviews on this topic see
2. F. Spindler, H.-U. Blaser, in Transition Metals for Organic Synthesis, 2nd ed., Vol. 2 (Eds.:, M. Beller, C. Bolm,), Wiley-VCH, Weinheim, 2004, p. 113
3. H.-U. Blaser, F. Spindler, in Handbook of Homogeneous Hydrogenation, Vol. 3 (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007, p. 1193
4. M. J. Palmer, M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045 - 2061
5. H.-U. Blaser, C. Malan, B. Pugin, F. Spinder, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103 - 151
6. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029 - 3069
7. T. C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753 - 819
8. M. Rüping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852 - 865.
9. For use of Ti and Zr catalysts see
10. C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1992, 114, 7562 - 7564
11. C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8952 - 8965
12. X. Verdaguer, U. E. W. Langer, S. L. Buchwald, Angew. Chem. 1998, 110, 1174 - 1178
13. Angew. Chem. Int. Ed. 1998, 37, 1103 - 1107
14. M. Ringwald, R. Stürmer, H. H. Brintzinger, J. Am. Chem. Soc. 1999, 121, 1524 - 1527
15. M. C. Hansen, S. L. Buchwald, Org. Lett. 2000, 2, 713 - 715
16. J. Yun, S. L. Buchwald, J. Org. Chem. 2000, 65, 767 - 774.
17. For use of Cu catalysts see:, B. H. Lipshutz, H. Shimizu, Angew. Chem. 2004, 116, 2278 - 2280
18. Angew. Chem. Int. Ed. 2004, 43, 2228 - 2230.
19. For use of Zn catalysts see:, B.-M. Park, S. Mun, J. Yun, Adv. Synth. Catal. 2006, 348, 1029 - 1032.
20. For use of Ru catalysts see
21. W. Oppolzer, M. Wills, M. Starkemann, G. Bernardinelli, Tetrahedron Lett. 1990, 31, 4117 - 4120
22. N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 4916 - 4917
23. K. Abdur-Rashid, A. J. Lough, R. H. Morris, Organometallics 2001, 20, 1047 - 1049
24. C. J. Cobley, J. P. Henschke, Adv. Synth. Catal. 2003, 345, 195 - 201
25. D. Guijarro, á. Pablo, M. Yus, Tetrahedron Lett. 2009, 50, 5386 - 5388.
26. For use of Rh complexes see
27. A. G. Becalski, W. R. Cullen, M. D. Fryzuk, B. R. James, G.-J. Kang, S. R. Rettig, Inorg. Chem. 1991, 30, 5002 - 5008
28. M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266 - 6267
29. J. Mao, D. C. Baker, Org. Lett. 1999, 1, 841 - 843
30. F. Spindler, H.-U. Blaser, Adv. Synth. Catal. 2001, 343, 68 - 70
31. R. Kadyrov, T. H. Riermeier, Angew. Chem. 2003, 115, 5630 - 5632
32. Angew. Chem. Int. Ed. 2003, 42, 5472 - 5474
33. G. Shang, Q. Yang, X. Zhang, Angew. Chem. 2006, 118, 6508 - 6510
34. Angew. Chem. Int. Ed. 2006, 45, 6360 - 6362.
35. For use of Pd catalysts see
36. H. Abe, H. Amii, K. Uneyama, Org. Lett. 2001, 3, 313 - 315
37. Q. Yang, G. Shang, W. Gao, J. Deng, X. Zhang, Angew. Chem. 2006, 118, 3916 - 3919
38. Angew. Chem. Int. Ed. 2006, 45, 3832 - 3835
39. Y.-Q. Wang, S.-M. Lu, Y.-G. Zhou, J. Org. Chem. 2007, 72, 3729 - 3734.
40. For use of Re complexes see:, K. A. Nolin, R. W. Ahn, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 12462 - 12463.
41. For applications of Ir catalysts see
42. F. Spindler, B. Pugin, H.-U. Blaser, Angew. Chem. 1990, 102, 561 - 562
43. Angew. Chem. Int. Ed. Engl. 1990, 29, 558 - 559
44. A. Togni, Angew. Chem. 1996, 108, 1581 - 1583
45. Angew. Chem. Int. Ed. Engl. 1996, 35, 1475 - 1477
46. R. Sablong, J. A. Osborn, Tetrahedron: Asymmetry 1996, 7, 3059 - 3062
47. G. Zhu, X. Zhang, Tetrahedron: Asymmetry 1998, 9, 2415 - 2418
48. C. Bianchini, P. Barbaro, G. Scapacchi, E. Farnetti, M. Graziani, Organometallics 1998, 17, 3308 - 3310
49. D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533 - 3536
50. Angew. Chem. Int. Ed. 2001, 40, 3425 - 3428
51. X.-B. Jiang, A. J. Minnaard, B. Hessen, B. L. Feringa, A. L. L. Duchateau, J. G. O. Andrien, J. A. Boogers, J. G. de Vries, Org. Lett. 2003, 5, 1502 - 1506
52. E. Guiu, B. Muñoz, S. Castillon, C. Claver, Adv. Synth. Catal. 2003, 345, 169 - 171
53. C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736 - 7739
54. Angew. Chem. Int. Ed. 2005, 44, 7564 - 7567
55. T. Imamoto, N. Iwadate, K. Yoshida, Org. Lett. 2006, 8, 2289 - 2292
56. M. T. Reetz, O. Bondarev, Angew. Chem. 2007, 119, 4607 - 4610
57. Angew. Chem. Int. Ed. 2007, 46, 4523 - 4526
58. C. Li, C. Wang, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450 - 14451
59. C. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967 - 6969
60. S. Shirai, H. Nara, Y. Kayaki, T. Ikariya, Organometallics 2009, 28, 802 - 809
61. Z. Han, Z. Wang, X. Zhang, K. Ding, Angew. Chem. 2009, 121, 5449 - 5453
62. Angew. Chem. Int. Ed. 2009, 48, 5345 - 5349
63. W. Li, G. Hou, M. Chang, X. Zhang, Adv. Synth. Catal. 2009, 351, 3123 - 3127
64. N. Mršić, A. J. Minnaard, B. L. Feringa, J. G. de Vries, J. Am. Chem. Soc. 2009, 131, 8358 - 8359
65. G. Hou, F. Gosselin, W. Li, J. C. McWilliams, Y. Sun, M. Weisel, P. D. OShea, C.-Y. Chen, I. W. Davies, X. Zhang, J. Am. Chem. Soc. 2009, 131, 9882 - 9883
66. A. Beaza, A. Pfaltz, Chem. Eur. J. 2010, 16, 4003 - 4009.
67. For use of organocatalysts see
68. S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590 - 7593
69. Angew. Chem. Int. Ed. 2005, 44, 7424 - 7427
70. S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13074 - 13075
71. R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84 - 86
72. G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830 - 5831.
73. For selected reviews on iron catalysis see
74. C. Bolm, J. Legros, J. L. Paith, L. Zani, Chem. Rev. 2004, 104, 6217 - 6254
75. S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363 - 3367
76. Angew. Chem. Int. Ed. 2008, 47, 3317 - 3321
77. A. Correa, O. G. Mancheño, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108 - 1117
78. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500 - 1511
79. R. H. Morris, Chem. Soc. Rev. 2009, 38, 2282 - 2291.
80. Selected reports on iron-catalyzed reactions from our group
81. I. Iovel, K. Mertins, J. Kischel, A. Zapf, M. Beller, Angew. Chem. 2005, 117, 3981 - 3985
82. Angew. Chem. Int. Ed. 2005, 44, 3913 - 3917
83. J. Kischel, I. Jovel, K. Mertins, A. Zapf, M. Beller, Org. Lett. 2006, 8, 19 - 22
84. S. Enthaler, G. Erre, M. K. Tse, K. Junge, M. Beller, Tetrahedron Lett. 2006, 47, 8095 - 8099
85. S. Enthaler, B. Hagemann, G. Erre, K. Junge, M. Beller, Chem. Asian J. 2006, 1, 598 - 604
86. G. Anilkumar, B. Bitterlich, F. G. Gelalcha, M. K. Tse, M. Beller, Chem. Commun. 2007, 289 - 291
87. F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M. K. Tse, M. Beller, Angew. Chem. 2007, 119, 7431 - 7435
88. Angew. Chem. Int. Ed. 2007, 46, 7293 - 7296
89. F. Shi, M. K. Tse, M.-M. Pohl, A. Brückner, S. Zhang, M. Beller, Angew. Chem. 2007, 119, 9022 - 9024
90. Angew. Chem. Int. Ed. 2007, 46, 8866 - 8868
91. K. M. Driller, H. Klein, R. Jackstell, M. Beller, Angew. Chem. 2009, 121, 6157 - 6160
92. Angew. Chem. Int. Ed. 2009, 48, 6041 - 6044
93. S. Zhou, K. Junge, D. Addis, S. Das, M. Beller, Angew. Chem. 2009, 121, 9671 - 9674
94. Angew. Chem. Int. Ed. 2009, 48, 9507 - 9510
95. S. Zhou, D. Addis, S. Das, K. Junge, M. Beller, Chem. Commun. 2009, 4883 - 4885
96. K. Junge, B. Wendt, N. Shaikh, M. Beller, Chem. Commun. 2010, 46, 1769 - 1771.
97. H. Nishiyama, A. Furuta, Chem. Commun. 2007, 760 - 762
98. N. S. Shaikh, S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 2531 - 2535
99. Angew. Chem. Int. Ed. 2008, 47, 2497 - 2501
100. B. K. Langlotz, H. Wadepohl, L. H. Gade, Angew. Chem. 2008, 120, 4748 - 4752
101. Angew. Chem. Int. Ed. 2008, 47, 4670 - 4674.
102. J.-S. Chen, L.-L. Chen, Y. Xing, G. Chen, W.-Y. Shen, Z.-R. Dong, Y.-Y. Dong, Y.-Y. Li, J.-X. Gao, Acta Chim. Sin. 2004, 62, 1745 - 1750
103. A. M. Tondreau, J. M. Darmon, B. M. Wile, S. K. Floyd, E. Lobkovsky, P. J. Chrik, Organometallics 2009, 28, 3928 - 3940
104. C. Sui-Seng, F. Freutel, A. J. Lough, R. H. Morris, Angew. Chem. 2008, 120, 954 - 957
105. Angew. Chem. Int. Ed. 2008, 47, 940 - 943
106. N. Meyer, A. J. Lough, R. H. Morris, Chem. Eur. J. 2009, 15, 5605 - 5610
107. A. Mikhailine, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2009, 131, 1394 - 1395
108. C. Sui-Seng, F. N. Haque, A. Hadzovic, A.-M. Pütz, V. Reuss, N. Meyer, A. J. Lough, M. Z.-D. Luliis, R. H. Morris, Inorg. Chem. 2009, 48, 735 - 743.
109. W. Krzyanowska, J. Stec, Synthesis 1982, 270 - 273
110. C. Bolm, M. Felder, Synlett 1994, 655 - 656
111. R. Giuliano, V. E. Manetta, G. R. Smith, Carbohydr. Res. 1995, 278, 345 - 350
112. S. Masumoto, H. Usuda, M. Suzuki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 5634 - 5635
113. J. Huang, X. Liu, Y. Wen, B. Qin, X. Feng, J. Org. Chem. 2007, 72, 204 - 208.
114. J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087 - 1089
115. J.-X. Gao, X.-D. Yi, P.-P. Xu, C.-L. Tang, H.-L. Wan, T. Ikariya, J. Organomet. Chem. 1999, 592, 290 - 295
116. J.-X. Gao, H. Zhang, X.-D. Yi, P.-P. Xu, C.-L. Tang, H.-L. Wang, K.-R. Tsai, T. Ikariya, Chirality 2000, 12, 383 - 388
117. H. Zhang, C.-B. Yang, Y.-Y. Li, Z.-R. Donga, J.-X. Gao, H. Nakamura, K. Murata, T. Ikariya, Chem. Commun. 2003, 142 - 143
118. Z.-R. Dong, Y.-Y. Li, J.-S. Chen, B.-Z. Li, Y. Xing, J.-X. Gao, Org. Lett. 2005, 7, 1043 - 1045
119. Y. Xing, J.-S. Chen, Z.-R. Dong, Y.-Y. Li, J.-X. Gao, Tetrahedron Lett. 2006, 47, 4501 - 4503.