Asymmetric transfer hydrogenation of imines and ketones using chiral RuIICl(η6-p-cymene)[(S, S)-N-TsDPEN as a catalyst: A computational study

Organometallics

Volumn 30, Issue 18, 2011, Pages 4822-4829

  Václavík, Jiří ^a   Kuzma, Marek ^b   Přech, Jan ^a   Kačer, Petr ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONES; ASYMMETRIC TRANSFER HYDROGENATION; CHIRAL CATALYST; COMPUTATIONAL STUDIES; ENERGY MINIMA; EXPERIMENTAL OBSERVATION; IONIC MECHANISMS; MOLECULAR SYSTEMS; P-CYMENE; P-CYMENE LIGANDS; PROTONATED; TRANSITION STATE; TRANSITION STATE GEOMETRY; TRANSITION STATE STRUCTURE;

CATALYSTS; DENSITY FUNCTIONAL THEORY; KETONES; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS;

HYDROGENATION;

EID: 79960785091     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200263d     Document Type: Article

References (25)

1. Andrews, I.; Cui, J.; DaSilva, J.; Dudin, L.; Dunn, P.; Hayler, J.; Hinkley, B.; Hughes, D.; Kaptein, B.; Kolis, S.; Lorenz, K.; Mathew, S.; Rammeloo, T.; Wang, L.; Wells, A.; White, T.; Xie, C.; Zhang, F. Org. Process Res. Dev. 2009, 13, 397
2. Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916
3. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521
4. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97
5. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931
6. Martins, J. E. D.; Clarkson, G. J.; Wills, M. Org. Lett. 2009, 11, 847
7. Åberg, J. B.; Samec, J. S. M.; Bäckvall, J.-E. Chem. Commun. 2006, 2771
8. Blackmond, D. G.; Ropic, M.; Stefinovic, M. Org. Process Res. Dev. 2006, 10, 457
9. Fleury-Brégeot, N.; de la Fuente, V.; Castillón, S.; Claver, C. ChemCatChem 2010, 2, 1346
10. Sandoval, C. A.; Ohkuma, T.; Utsumi, N.; Tsutsumi, K.; Murata, K.; Noyori, R. Chem. Asian J. 2006, 1-2, 102
11. Sandoval, C. A.; Bie, F.; Matsuoka, A.; Yamaguchi, Y.; Naka, H.; Li, Y.; Kato, K.; Utsumi, N.; Tsutsumi, K.; Ohkuma, T.; Murata, K.; Noyori, R. Chem. Asian J. 2010, 5, 806
12. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285
13. Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466
14. For an exhaustive review on computational solvation models, see this review: Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
15. See e.g.: Balcells, D.; Maseras, F. New J. Chem. 2007, 31, 333
16. Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem., Int. Ed. 2001, 40, 2818
17. MacNeil, P. A.; Roberts, N. K.; Bosnich, B. J. Am. Chem. Soc. 1981, 103, 2273
18. Gulamhussen, A. M.; Kačer, P.; Přech, J.; Kuzma, M.; Červený, L. React. Kinet. Catal. Lett. 2009, 97, 335
19. Soni, R.; Cheung, F. K.; Clarkson, G. C.; Martins, J. E. D.; Graham, M. A.; Wills, M. Org. Biomol. Chem. 2011, 9, 3290
20. Frisch, M. J.; Gaussian 03, revision E.01; Gaussian, Inc., Wallingford, CT, 2004.
21. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc., Wallingford, CT, 2009.
22. Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785-789
23. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
24. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
25. Fukui, K. Acc. Chem. Res. 1981, 14, 363