New C2-symmetric bis(sulfonamide)-cyclohexane-1,2-diamine-RhCp* complex and its application in the asymmetric transfer hydrogenation (ATH) of ketones in water

Tetrahedron Letters

Volumn 47, Issue 48, 2006, Pages 8515-8518

  Cortez, Norma A ^a   Rodríguez Apodaca, Ramón ^a   Aguirre, Gerardo ^a   Parra Hake, Miguel ^a   Cole, Thomas ^b   Somanathan, Ratnasamy ^a  

^a TIJUANA INSTITUTE OF TECHNOLOGY   (Mexico)

^b SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

Asymmetric transfer hydrogenation; Bis(sulfonamide) ligands; Ketones; RhCp* complex

Indexed keywords

2 PROPANOL; ALCOHOL; CYCLOHEXANE DERIVATIVE; DIAMINE DERIVATIVE; FORMIC ACID; HYDROGEN; KETONE; POTASSIUM HYDROXIDE; RHODIUM COMPLEX; SULFONAMIDE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHIRALITY; COMPLEX FORMATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; REDUCTION KINETICS;

EID: 33750294019     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.141     Document Type: Article

References (54)

1. In: Collins A.N., Sheldrake G.N., and Crosby J. (Eds). Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds (1992), John Wiley & Sons, Chichester
2. Hett R., Senanayake C.H., and Wald S.A. Tetrahedron Lett. 39 (1998) 1705-1708
3. Wang G., Liu X., and Zhao G. Tetrahedron: Asymmetry 16 (2005) 1873-1879
4. Zhu D., Mukherjee C., and Hua L. Tetrahedron: Asymmetry 16 (2005) 3275-3278
5. Lennon I.C., and Ramsden J.A.. Org. Process. Res. Dev. 9 (2005) 110-112
6. Reilly M., Anthony D.R., and Gallagher C. Tetrahedron Lett. 44 (2003) 2927-2930
7. Okano K., Murata K., and Ikariya T. Tetrahedron Lett. 41 (2000) 9277-9280
8. Cederbaum F., Lamberte C., Malan C., Naud F., Spindler F., Struder M., and Blazer H.-U. Adv. Synth. Catal. 346 (2004) 842-848
9. Hennig M., Püntener K., and Scalone M. Tetrahedron: Asymmetry 11 (2000) 1849-1858
10. Noyori R., and Hashiguchi S. Acc. Chem. Res. 30 (1997) 97-102
11. Hamada T., Torri T., Onishi T., Izawa K., and Ikariya T. J. Org. Chem. 69 (2004) 7391-7394
12. Hamada T., Torii T., Onishi T., Izawa K., and Ikariya T. Tetrahedron 60 (2004) 7411-7417
13. Hamada T., Torii T., Izawa K., Noyori R., and Ikariya T. Org. Lett. 4 (2002) 4373-4376
14. Watanabe M., Murata K., and Ikariya T. J. Org. Chem. 67 (2002) 1712-1715
15. Koike T., Murata K., and Ikariya T. Org. Lett. 2 (2000) 3833-3836
16. Noyori R. Adv. Synth. Catal. 345 (2003) 15-32
17. Noyori R., Yamakawa M., and Hashiguchi S. J. Org. Chem. 66 (2001) 7931-7944
18. Yamakawa M., Ito H., and Noyori R. J. Am. Chem. Soc. 122 (2000) 1466-1478
19. Ikariya T., Murata K., and Noyori R. Org. Biomol. Chem. 4 (2006) 393-406
20. Recent reviews:. Gladiali S., and Alberico E. Chem. Soc. Rev. 35 (2006) 226-236
21. Samec J.S.M., Bäckvall J.-E., Andersson P.G., and Brandt P. Chem. Soc. Rev. 35 (2006) 237-248
22. Wu X., Vinci D., Ikariya T., and Xiao J. Chem. Commun. (2005) 4447-4449
23. Earlier examples of diamino ligands:. Chen Y.C., Wu T.F., Deng J.G., Liu H., Jiang Y.Z., Choi M.C.K., and Chan A.C.S. Chem. Commun. (2001) 1488-1489
24. Ros A., Magriz A., Dietrich H., Fernández R., Ava E., and Lassaletta J.M. Org. Lett. 8 (2006) 127-130
25. Fukuzawa S.-I., and Suzuki T. Eur. J. Org. Chem. (2006) 1012-1016
26. Yamashita M., and Ohta S. Chem. Commun. (2005) 2134-2136
27. Wang F., Liu H., Cun L., Zhu J., Deng J., and Jiang Y. J. Org. Chem. 70 (2005) 9424-9429
28. Li X., Wu X., Chen W., Hancock F.E., King F., and Xiao J. Org. Lett. 6 (2004) 3321-3324
29. Wu X., Li X., Hems W., King F., and Xiao J. Chem. Commun. (2004) 1818-1819
30. Liu P.N., Deng J.G., Tu Y.Q., and Wang S.H. Chem. Commun. (2004) 2070-2071
31. Schlatter A., Kundu M.K., and Woggon W.-D. Angew. Chem., Int. Ed. 43 (2004) 6731-6734
32. Xing Y., Chen J.-S., Dong Z.-R., Li Y.-Y., and Gao J.-X. Tetrahedron Lett. 47 (2006) 4501-4503
33. Matsunga H., Ishizuka T., and Kunieda T. Tetrahedron Lett. 46 (2005) 3645-3648
34. Ma Y., Liu H., Chen L., Cui X., Zhu J., and Deng J.G. Org. Lett. 5 (2003) 2103-2106
35. Peach P., Cross D.J., Kenny J.A., Mann I., Houson I., Campbell L., Walsgrove T., and Wills M. Tetrahedron 62 (2006) 1864-1876
36. Västilä P., Wettergreen J., and Adolfsson H. Chem. Commun. (2005) 4039-4041
37. Cheung F.K., Hayes A.M., Hannedouche J., Yim A.S.Y., and Wills M. J. Org. Chem. 70 (2005) 3188-3197
38. Mao J., Wan B., Wu F., and Lu S. Tetrahedron Lett. 46 (2005) 7341-7344
39. Reetz M.T., and Xiaoguang L. J. Am. Chem. Soc. 128 (2006) 1044-1045
40. Guo R., Elpelt C., Chen X., Song D., and Morris R.H. Chem. Commun. (2005) 3050-3052
41. Yim A.S.Y., and Wills M. Tetrahedron 61 (2005) 7994-8004
42. Cabou J., Brocard J., and Pélinski L. Tetrahedron Lett. 46 (2005) 1185-1188
43. Tan D.-M., and Chan K.S. Tetrahedron Lett. 46 (2005) 503-505
44. Sortais J.-B., Ritleng V., Voelklin A., Holuigue A., Smail H., Barloy L., Sirlin C., Verzijl G.K.M., Boogers J.A.F., de Vries A.H.M., and Pfeffer M. Org. Lett. 7 (2005) 1247-1250
45. Murata K., Ikariya T., and Noyori R. J. Org. Chem. 64 (1999) 2186-2187
46. Sun X., Manos G., Blacker J., Martin J., and Gavriilidis A. Org. Process Res. Dev. 8 (2004) 909-914
47. Matharu D.S., Morris D.J., Kawamoto A.M., Clarkson G.J., and Wills M. Org. Lett. 7 (2005) 5489-5491
48. Hayes A., Morris D.J., Clarkson G.J., and Wills M. J. Am. Chem. Soc. 127 (2005) 7318-7319
49. Sammis G.M., Danjo H., and Jacobsen E.N. J. Am. Chem. Soc. 126 (2004) 9928-9929
50. Flores-López C.Z., Flores-López L.Z., Aguirre G., Hellberg L.H., Parra-Hake M., and Somanathan R. J. Mol. Catal. A: Chem. 215 (2004) 73-79
51. Cortez N.A., Rodríguez- Apodaca R., Flores-López L.Z., Parra-Hake M., and Somanathan R. ARKIVOC VI (2005) 162-171
52. Schanz H.-J., Linseis M., and Gilheany D.G. Tetrahedron: Asymmetry 14 (2003) 2763-2769
53. Ng K., Somanathan R., and Walsh P.J. Tetrahedron: Asymmetry 12 (2001) 1719-1722
54. Püntener K., Schwinl L., and Knochel P. Tetrahedron Lett. 37 (1996) 8165-8168