Ru(II) complexes of N-Alkylated TsDPEN ligands in asymmetric transfer hydrogenation of ketones and imines

Organic Letters

Volumn 11, Issue 4, 2009, Pages 847-850

  Martins, José E D ^a   Clarkson, Guy J ^a   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 64349112343     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802801p     Document Type: Article

References (46)

1. (a) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
2. (b) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
3. (c) Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201.
4. (d) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
5. (e) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.
6. (f) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
7. (g) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300.
8. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
9. (b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
10. (c) Matsumura, K.; Hashiguchi; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
11. (d) Murata, K.; Okano, K.; Miyagi, M.; Iwane, H.; Noyori, R.; Ikariya, T. Org. Lett. 1999, 1, 1119.
12. (e) Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1997, 36, 285.
13. (a) Cross, D. J.; Kenny, J. A.; Houson, I.; Campbell, L.; Walsgrove, T.; Wills, M. Tetrahedron: Asymmetry 2001, 12, 1801.
14. (b) Hamada, T.; Torii, T.; Izawa, K.; Noyori, R.; Ikariya, T. Org. Lett. 2002, 4, 4373.
15. (c) Hamada, T.; Torii, T.; Izawa, K.; Ikariya, T. Tetrahedron 2004, 60, 7411.
16. (d) Hamada, T.; Torii, T.; Onishi, T.; Izawa, K.; Ikariya, T. Org. Lett. 2004, 69, 7391.
17. (e) Thorpe, T.; Blacker, J.; Brown, S, M.; Bubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041.
18. (f) Wu, X.; Vinci, D.; Ikariya, T.; Xiao, J. Chem. Commun. 2005, 4447.
19. (a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916.
20. (b) Wills, M. In Modern Reduction Methods; Andersson, P. G., Munslow, I. J., Eds.; Wiley-VCH: Weinheim, 2008; Chapter 1, pp 271-296.
21. (c) Williams, G. D.; Wade, C. E.; Wills, M. Chem. Commun. 2005, 4735.
22. (a) Mao, J.; Baker, D. C. Org. Lett. 1999, 1, 841.
23. (b) Blacker, J.; Martin, J. Scale up studies in asymmetric transfer hydrogenation. In Asymmetric Catalysis on an Industrial Scale: Challenges, Approaches and Solutions; Blaser, H. U., Schmidt, E., Eds.; Wiley: New York, 2004; pp 201-216.
24. (c) Sun, X.; Manos, G.; Blacker, J.; Martin, J.; Gavriilidis, A. Org. Proc. Res. Dev. 2004, 8, 909.
25. (a) Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem. Int. Ed. 2001, 40, 2818.
26. (b) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931.
27. (c) Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
28. (d) Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.
29. (e) Brandt, P.; Roth, P.; Andersson, P. G. J. Org. Chem. 2004, 69, 4885.
30. (a) Aberg, J. B.; Samec, J. S. M.; Bäckvall, J.-E. Chem. Commun. 2006, 2771-2773.
31. (b) Casey, C. P.; Clark, T. B.; Guzei, I. A. J. Am. Chem. Soc. 2007, 129, 11821-11827.
32. (c) Blackmond, D. G.; Ropic, M.; Stefinvic, M. Org. Proc. Res. Dev. 2006, 10, 457.
33. (d) Samec, J. S. M.; Ell, A. H.; Aberg, J. B.; Primalov, T.; Eriksson, L.; Bäckvall, J.-E. J. Am. Chem. Soc. 2006, 128, 14293.
34. (e) Casey, C. P.; Johnson, J. B. J. Am. Chem. Soc. 2005, 127, 1883.
35. (a) Koike, T.; Ikariya, T. Adv. Synth. Catal. 2004, 346, 37.
36. (b) Koike, T.; Ikariya, T. J. Organomet. Chem. 2007, 692, 408.
37. (a) Cortez, N. A.; Rodriguez-Apodaca, R.; Aguirre, G.; Parra-Hake, M.; Cole, T.; Somanathan, R. Tetrahedron Lett. 2006, 47, 8515-8518.
38. (b) Cortez, N. A.; Flores-Lopez, C. Z.; Rodriguez-Apodaca, R.; Flores-Lopez, L. Z.; Parra-Hake, M.; Somanathan, R. ARKIVOC 2005, 6, 162.
39. (c) Canivet, J.; Süss-Fink, G. Green Chem. 2007, 9, 391-397.
40. (d) Dahlin, N.; Bøgevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004, 346, 1101.
41. Xue, D.; Chen, Y.-C.; Cui, X.; Wang, Q.-W.; Zhu, J.; Deng, J.-G J. Org. Chem. 2005, 70, 3584.
42. Hayes, A. M.; Morris, D. J.; Clarkson, G J.; Wills, M. J. Am. Chem. Soc. 2005, 127, 7318.
43. Martins, J. E. D.; Morris, D. J.; Wills, M. Tetrahedron Lett. 2009, 50, 688-692. An attempt to prepare the N'- neopentylTsDPEN derivative was unsuccessful, possibly for reasons of steric hindrance.
44. (a) Tietze, L. F.; Zhou, Y.; Topken, E. Eur. J. Org. Chem. 2000, 2247.
45. (b) Vedej, E.; Trapencieris, P.; Suna, E. J. Org. Chem. 1999, 64, 6724.
46. Cheung, F. K.; Lin, C.; Mnissi, F.; Criville, A. L.; Graham, M. A.; Fox, D. J.; Wills, M. Org Lett. 2007, 9, 4659. (15) Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.