Iridium diamine catalyst for the asymmetric transfer hydrogenation of ketones

Angewandte Chemie - International Edition

Volumn 50, Issue 38, 2011, Pages 8979-8981

  Vázquez Villa, Henar ^a   Reber, Stefan ^a   Ariger, Martin A ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

asymmetric catalysis; hydrogen transfer; iridium; ketones; water

Indexed keywords

AROMATIC ALCOHOLS; ASYMMETRIC CATALYSIS; ASYMMETRIC TRANSFER HYDROGENATION; CHIRAL LIGAND; DIAMINE COMPLEXES; DIAMINE LIGANDS; HYDROGEN TRANSFER;

CATALYSTS; ENANTIOSELECTIVITY; HYDROGENATION; IRIDIUM; KETONES; LIGANDS; ORGANIC COMPOUNDS;

IRIDIUM COMPOUNDS;

EID: 80052586215     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102732     Document Type: Article

References (42)

1. T. Ikariya, K. Murata, R. Noyori, Org. Biomol. Chem. 2006, 4, 393
2. S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226
3. J. S. M. Samec, J.-E. Bäckvall, G. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237
4. K. Everaere, A. Mortreux, J.-F. Carpentier, Adv. Synth. Catal. 2003, 345, 67
5. H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103
6. C. Wang, X. Wu, J. Xiao, Chem. Asian J. 2008, 3, 1750. For a recent review on Ir-catalyzed ATH see
7. O. Saidi, M. J. Williams, Topics in Organometallic Chemistry, Vol. 34 (Ed.:, P. G. Andersson,), Springer, Heidelberg, 2011, 77.
8. K. Matsumura, S. Sashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738
9. A. Fujii, N. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521
10. S. Hashiguchi, A. Fujii, J. Takehara, T. Akariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562.
11. Y. Li, Z. Li, W. Li, Q. Wang, F. Tao, Org. Biomol. Chem. 2005, 3, 2513
12. P. N. Liu, P. M. Gu, F. Wang, Y. Q. Tu, Org. Lett. 2004, 6, 169
13. M. Watanabe, K. Murata, T. Ikayriya, J. Org. Chem. 2002, 67, 1712
14. D. S. Matharu, D. J. Morris, G. Y. Clarkson, M. Wills, Chem. Commun. 2006, 3232
15. A. Zaitsev, H. Adolfsson, Org. Lett. 2006, 8, 5129-5132
16. X. Wu, X. Li, F. King, J. Xiao, Angew. Chem. 2005, 117, 3473
17. Angew. Chem. Int. Ed. 2005, 44, 3407
18. J. Hannedouche, G. Y. Clarkson, M. Wills, J. Am. Chem. Soc. 2004, 126, 986
19. D. Återk, M. S. Stephan, B. Mohar, Tetrahedron Lett. 2004, 45, 535
20. X. Li, X. Wu, W. Chen, F. E. Hancock, F. King, J. Xiao, Org. Lett. 2004, 6, 3321
21. Y. Ma, H. Liu, L. Chen, X. Cui, J. Zhu, J. Deng, Org. Lett. 2003, 5, 2103.
22. S. Ogo, K. Uehara, T. Abura, S. Fukuzumi, J. Am. Chem. Soc. 2004, 126, 3020
23. T. Abura, S. Ogo, Y. Watanabe, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 4149
24. S. Ogo, N. Makihara, Y. Kaneko, Y. Watanabe, Organometallics 2001, 20, 4903
25. S. Ogo, N. Makihara, Y. Watanabe, Organometallics 1999, 18, 5470.
26. X. Li, J. Blacker, I. Houson, X. Wu, J. Xiao, Synlett 2006, 1155
27. W. Wu, D. Vinci, T. Ikariya, J. Xiao, Chem. Commun. 2005, 4447; For an example of iridium (III) catalyst for the TH of aldehydes, see
28. X. Wu, J. Liu, X. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. Ruan, J. Xiao, Angew. Chem. 2006, 118, 6870
29. Angew. Chem. Int. Ed. 2006, 45, 6718.
30. F. Wang, H. Liu, L. Cun, J. Zhu, J. Deng, Y. Jiang, J. Org. Chem. 2005, 70, 9424.
31. Z.-R. Dong, Y.-Y. Li, J.-S. Chen, B.-Z. Li, Y. Xing, J.-X. Gao, Org. Lett. 2005, 7, 1043
32. T. Thorpe, J. Blacker, S. M. Brown, C. Bubert, J. Crosby, S. Fitzjohn, J. P. Muxworthy, J. M. J. Williams, Tetrahedron Lett. 2001, 42, 4041
33. K. Murata, T. Ikariya, R. Noyori, J. Org. Chem. 1999, 64, 2186
34. K. Mashima, T. Abe, K. Tani, Chem. Lett. 1998, 1199
35. O. Soltani, M. A. Ariger, E. M. Carreira, Org. Lett. 2009, 11, 4196
36. O. Soltani, M. A. Ariger, H. Vázquez-Villa, E. M. Carreira, Org. Lett. 2010, 12, 2893
37. S. Arita, T. Koike, Y. Kayaki, T. Ikariya, Angew. Chem. 2008, 120, 2481
38. Angew. Chem. Int. Ed. 2008, 47, 2447.
39. For a review of recent advances in asymmetric hydrosilylation, transfer hydrogenation, and hydrogenation of ketones catalyzed by iridium complexes, see:, R. Malacea, R. Poli, E. Manouri, Coord. Chem. Rev. 2010, 254, 729.
40. For a discussion of asymmetric transfer hydrogenation in water with Pt group metal catalysts, see:, X. Wu, C. Wang, J. Xiao, Platinum Met. Rev. 2010, 54, 3.
41. Amino alcohols have been examined in asymmetric transfer hydrogenation of acetophenones, affording phenethyl alcohols in 35-87 % ee, see:, X. Wu, X. Li, M. McConville, O. Saidi, J. Xiao, J. Mol. Catal. A 2006, 247, 153.
42. Aminosulfoxides have been reported as ligands for Ir in asymmetric transfer hydrogenation of acetophenone, see:, D. G. I. Petra, P. C. J. Kramer, A. L. Spek, H. E. Schoemaker, P. W. N. M. van Leeuwen, J. Org. Chem. 2000, 65, 3010.