Iridium-catalyzed enantioselective hydrogenation of cyclic imines

Advanced Synthesis and Catalysis

Volumn 352, Issue 18, 2010, Pages 3121-3125

  Chang, Mingxin ^a   Li, Wei ^a   Hou, Guohua ^a   Zhang, Xumu ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

asymmetric catalysis; cyclic imines; enantioselectivity; hydrogenation; iridium

Indexed keywords

EID: 78650355083     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000473     Document Type: Article

References (44)

1. A. R. Pinder, Nat. Prod. Rep. 1992, 9, 17
2. J. P. Michael, Nat. Prod. Rep. 1991, 8, 563.
3. S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069
4. H.-U. Blaser, C. Malan, B. Pugin, F. Spinder, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103.
5. T. Spangenberg, B. Breit, A. Mann, Org. Lett. 2009, 11, 261.
6. J. Lloyd, H. J. Finlay, W. Vacarro, T. Hyunh, A. Kover, R. Bhandaru, L. Yan, K. Atwal, M. L. Conder, T. Jenkins-West, H. Shi, C. Huang, D. Li, H. Sun, P. Levesque, Bioorg. Med. Chem. 2010, 20, 1436.
7. A. K. Amegadzie, K. M. Gardinier, E. J. Hembre, P. A. Hipskind, L. N. Jungheim, B. S. Muehl, K. A. Savin, K. J. Thrasher, S. A. Boyd, (Lilly), Patent WO 2005000821 A1, 2005.
8. C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736
9. Angew. Chem. Int. Ed. 2005, 44, 7564
10. T. Imamoto, N. Iwadate, K. Yoshida, Org. Lett. 2006, 8, 2289
11. S.-F. Zhu, J.-B. Xie, Y.-Z. Zhang, S. Li, Q.-L. Zhou, J. Am. Chem. Soc. 2006, 128, 12886
12. M. N. Cheemala, P. Knochel, Org. Lett. 2007, 9, 3089
13. C. Li, C. Wang, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450
14. H. Guan, M. Limura, M. P. Magee, J. R. Norton, G. Zhu, J. Am. Chem. Soc. 2005, 127, 7805
15. Z. Han, Z. Wang, X. Zhang, K. Ding, Angew. Chem. 2009, 121, 5449
16. Angew. Chem. Int. Ed. 2009, 48, 5345
17. G. Hou, F. Gosselin, W. Li, J. C. McWilliams, Y. Sun, M. Weisel, P. D. O'Shea, C. Chen, I. W. Davies, X. Zhang, J. Am. Chem. Soc. 2009, 131, 9882
18. W. Li, G. Hou, M. Chang, X. Zhang, Adv. Synth. Catal. 2009, 351, 3123
19. G. Hou, R. Tao, Y. Sun, X. Zhang, F. Gosselin, J. Am. Chem. Soc. 2010, 132, 2124
20. A. Baeza, A. Pfaltz, Chem. Eur. J. 2010, 16, 4003.
21. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029
22. rd edn., (Ed.:, I. Ojima,), Wiley, Hoboken, 2010, pp 343-436.
23. C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8952.
24. C. Li, J. Xiao, J. Am. Chem. Soc. 2008, 130, 13208.
25. C. J. Cobley, J. P. Henschke, Adv. Synth. Catal. 2003, 345, 195.
26. G.-J. Kang, W. R. Cullen, M. D. Fryzuk, B. R. James, J. P. Kutney, J. Chem. Soc. Chem. Commun. 1988, 1466
27. T. Morimoto, N. Nakajima, K. Achiwa, Chem. Pharm. Bull. 1994, 42, 1951
28. T. Morimoto, K. Achiwa, Tetrahedron: Asymmetry 1995, 6, 2661
29. T. Morimoto, N. Suzuki, K. Achiwa, Heterocycles 1996, 43, 1557
30. T. Morimoto, N. Suzuki, K. Achiwa, Tetrahedron: Asymmetry 1998, 9, 183
31. K. Tani, J.-I. Onouchi, T. Yamagata, Y. Kataoka, Chem. Lett. 1995, 955
32. G. Zhu, X. Zhang, Tetrahedron: Asymmetry 1998, 9. 2415.
33. Y. N. C. Chan, J. A. Osborn, J. Am. Chem. Soc. 1990, 112, 9400
34. R. Sablong, J. A. Osborn, Tetrahedron: Asymmetry 1996, 7, 3059
35. T. Yamagata, H. Tadaoka, M. Nagata, T. Hirao, Y. Kataoka, V. R. Vidal, J. P. Genêt, K. Mashima, Organometallics 2006, 25, 2505.
36. Q. Yang, G. Shang, W. Gao, J. Deng, X. Zhang, Angew. Chem. 2006, 118, 3916
37. Angew. Chem. Int. Ed. 2006, 45, 3832.
38. D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533
39. Angew. Chem. Int. Ed. 2001, 40, 3425.
40. K. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26
41. Angew. Chem. Int. Ed. 2002, 41, 26.
42. H.-U. Blaser, Adv. Synth. Catal. 2002, 344, 17.
43. C. A. Zezza, M. B. Smith, B. A. Ross, A. Arhin, P. L. E. Cronin, J. Org. Chem. 1984, 49, 4397
44. D. H. Hua, S. W. Miao, S. N. Bharathi, T. Katsuhira, A. A. Bravo, J. Org. Chem. 1990, 55, 3682.