N-N Torsion angle in BINAM-Mono and bis(sulfonamide) ligands and its effect on the Catalytic asymmetric transfer hydrogenation (ATH) of aromatic ketones

Journal of the Mexican Chemical Society

Volumn 55, Issue 1, 2011, Pages 16-20

  Barrón Jaime, Angélica ^a   Aguirre, Gerardo ^a   Parra Hake, Miguel ^a   Chávez, Daniel ^a   Madrigal, Domingo ^a,b   Sanders, Belynda ^b   Cooksy, Andrew L ^b   Somanathan, Ratnasamy ^a  

^a TIJUANA INSTITUTE OF TECHNOLOGY   (Mexico)

^b SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

Aqueous media; Asymmetric transfer hydrogenation; Complexes; Monosulfonamide ligands; RhIIICp

Indexed keywords

EID: 79956344229     PISSN: 1870249X     EISSN: 16659686     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Blacker, J.; Martin, J., in: Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions; Blaser, H. U.; Schmidt, E., Eds., Wiley-VCH, Weinheim, Germany, 2004.
2. Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds; Collins, A.N.; Sheldrake, G.N.; Crosby, J., Eds., John Wiley & Sons, Chichester, 1992.
3. Hett, R.; Senanayake, C. H.; Wald, S. A. Tetrahedron Lett. 1998, 39, 1705-1708.
4. Wang, G.; Liu, X.; Zhao, G. Tetrahedron: Asymmetry 2005, 16, 1873-1879.
5. Zhu, D.; Mukherjee, C.; Hua, L. Tetrahedron:Asymmetry 2005, 16, 3275-3278.
6. Lennon, I. C.; Ramsden, J. A. Org. Process. Res. Dev. 2005, 9, 110-112.
7. Reilly, M.; Anthony, D. R.; Gallagher, C. Tetrahedron Lett. 2003, 44, 2927-2930.
8. Okano, K.; Murata, K.; Ikariya, T. Tetrahedron Lett. 2000, 41, 9277-9280.
9. Cederbaum, F.; Lamberte, C.; Malan, C.; Naud, F.; Spindler, F.; Struder, M.; Blazer, H.-U. Adv. Synth. Catal. 2004, 346, 842-848.
10. Hennig, M.; Püntener, K.; Scalone, M. Tetrahedron: Asymmetry 2000, 11, 1849-1858.
11. Noyori's work: Noyori, R.; Kitamura, M.; Ohkuma, T. PNAS, 2004, 101, 5356-5362.
12. Noyori, R. Chem. Commun. 2005, 1807-1809.
13. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1997, 36, 285-288.
14. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
15. Marsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
16. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73 and references therein.
17. Noyori, R. Adv. Synth. Catal. 2003, 345, 15-32.
18. Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466-1478.
19. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
20. Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393-406.
21. Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226-236.
22. Samec, J. S. M.; Bäckvall, J.-E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006, 35, 237-248.
23. Wu, X.; Xiao, J. Chem. Comm. 2007, 2449-2466.
24. Liu, S.; Xiao, J. J. Mol. Cat. A. Chem. 2007, 270,1-43.
25. Cortez, N. A.; Rodríguez-Apodaca, R.; Aguirre, G.; Parra-Hake, M.; Cole, T.; Somanathan, R. Tetrahedron Lett. 2006, 47, 8515-8518.
26. Cortez, N. A.; Aguirre, G.; Parra-Hake, M.; Somanathan, R. Tetrahedron Lett. 2007, 48, 4335-4338.
27. Cortez, N. A.; Aguirre, G.; Parra-Hake, M.; Somanathan, R. Tetrahedron: Asymmetry 2008, 19, 1304-1309.
28. Wu, X.; Vinci, D.; Ikariya, T.; Xiao, J. Chem. Commun. 2005, 4447-4449.
29. Ma, Y.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. Org. Lett. 2003, 5, 2103-2106.
30. Ou, Z.; Wu, J.; Yang, L.; Cen, P. Korean J. Material Sci. Chem. Eng. 2008, 25, 124-128.
31. Chen, Y.-X.; Li, Y.-M.; Lam, K.-H.; Chan, A. S.-C. Chinese J. Chem. 2002, 20, 606-609.
32. Furegati, M.; Rippert, A. J. Tetrahedron: Asymmetry 2005, 16, 3947-3950.
33. Faller, J. W.; Fontaine, P. P. J. Organomet. Chem. 2007, 692, 1110-1117.
34. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
35. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
36. Dunning, J. T. H. J. Chem. Phys. 1989, 90, 1007-1023.
37. Kendall, R. A.; Dunning, J. T. H.; Harrison, R. A. J. Chem. Phys. 1992, 96, 6796-6806.
38. Woon, D. E.; Dunning, J. T. H. J. Chem. Phys. 1993, 98, 1358-1371.
39. Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612-630.
40. Grotjahn, D. B.; Zeng, X.; Cooksy, A. L.; Kassel, W. S.; Di-Pasquale, A. G.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2007, 26, 3385-3402.