A New Class of "Tethered" Ruthenium(II) Catalyst for Asymmetric Transfer Hydrogenation Reactions

Journal of the American Chemical Society

Volumn 126, Issue 4, 2004, Pages 986-987

  Hannedouche, Jérôme ^a   Clarkson, Guy J ^a   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

RUTHENIUM DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; COMPLEX FORMATION; HYDROGENATION; MOLECULAR STABILITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0742289188     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0392768     Document Type: Article

References (32)

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) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992. 92, 1051.
4. (a) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.-I.; Ikariya, T.; Noyori, R. Chem. Commun. 1996, 233.
5. (b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
6. (c) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
7. (d) Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
8. (e) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
9. (f) Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem., Int. Ed. 2001, 40, 2818.
10. Hamada, T.; Torii, T.; Izawa, K.; Noyori, R.; Ikariya, T. Org. Lett. 2002, 4, 4373.
11. (a) Nordin, S. J. M.; Roth, P.; Tarnai, T.; Alonso, D. A.; Brandt, P.; Andersson, P. G. Chem.-Eur. J. 2001, 7, 1431.
12. (b) Everaere, K.; Mortreux, A.; Bulliard, M.; Brussee, J.; van der Gen, A.; Nowogrocki, G.; Carpentier, J. F. Eur. J. Org. Chem. 2001, 275,
13. (c) Hennig, M.; Puntener, K.; Scalone, M. Tetrahedron: Asymmetry 2000, 11, 1849.
14. (d) Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO 98/42643 Al, 1998.
15. (e) Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2291.
16. (f) Langer, T.; Helmchen, G. Tetrahedron Lett. 1996. 37, 1381.
17. (g) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
18. (h) Perra, D. G. I.; Reek, J. N. H.; Handgraaf, J.-W.; Meijer, E. J.; Dierkes, P.; Kamer, P. C. J.; Brussee, J.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. Chem.-Eur. J. 2000, 6, 2818.
19. (i) Faller, J. W.; Lavoie, A. R. Organometallics 2002, 21, 2010.
20. (j) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199.
21. (a) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226.
22. (b) Hannedouche, J.; Kenny, J. A.; Walsgrove, T.; Wills, M. Synlett 2002, 263.
23. (c) Palmer, M. J.; Kenny, J. A.; Walsgrove, T.; Kawamoto, A. M.; Wills, M. J. Chem. Soc., Perkin Trans. 1 2002, 416.
24. Strictly, compounds 1 and 2 are catalyst precursors. The true catalytic species are formed by HCl elimination.
25. Related complexes with potential for forming a tether have been reported since the start of this project: (a) Soleimannejad, J.; Sisson, A.; White, C. Inorg. Chim. Acta 2003, 352, 121.
26. (b) Wendicke, S. B.; Burri, E. Scopelliti, R.; Severin. K. Organometallics 2003, 22, 1894.
27. Compounds 5 and 6 were synthesised respectively via the reductive coupling of 3-(cyclohexa-1,4-dienyl)propanal with (1R,2S) norephedrine and the reaction of (R,R)-1,2-diphenylethylenediamine and 2-(cyclohexa-1,4-dienyl)ethanesulfonyl chloride. See Supporting Information.
28. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233.
29. Miyaki, Y.; Onishi, T.; Kurosawa, H. Inorg. Chim. Acta 2000, 300-302, 369.
30. 6-mesitylene rather than unsubstituted benzene. In this study, a product of 98% ee was obtained from acetophenone.
31. The oxidized versions of 5 and 6 were synthesized in a similar manner using (3-bromo-propyl)benzene and 2-(phenyl)ethanesulfonyl chloride, respectively.
32. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.