Pyroglutamic acid as a chiral auxiliary in the diastereoselective hydrogenation of disubstituted aromatic rings on Rh(111): A periodic density functional theory approach

Journal of Catalysis

Volumn 217, Issue 1, 2003, Pages 23-29

  Barbosa, Luis Antonio M M ^a,b,c   Sautet, Philippe ^a,b  

^a CNRS   (France)

^b UNIVERSITÉ DE LYON   (France)

^c EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Chiral auxiliary; DFT; Diastereoselective hydrogenation; Rh(111)

Indexed keywords

AMINE; AROMATIC CARBOXYLIC ACID; NICOTINYL ALCOHOL; PYROGLUTAMIC ACID; RHODIUM COMPLEX;

ADSORPTION; ARTICLE; CATALYSIS; DIASTEREOISOMER; ENANTIOSELECTIVITY; HYDROGENATION; SURFACE PROPERTY; THEORY;

EID: 0042761215     PISSN: 00219517     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9517(03)00039-3     Document Type: Article

References (40)

1. Orito Y., Imai S. J. Chem. Soc. Jpn. 8:1979;118.
2. Schwalm O., Minder B., Weber J., Baiker A. Catal. Lett. 271:1994;279.
3. Singh U.K., Landau R.N., Sun Y., LeBlond C., Blackmond D.G., Tanielyan S.K., Augustine R.L. J. Catal. 154:1995;91.
4. Studer M., Burkhardt S., Blaser H.-U. Chem. Commun. 1999;1727.
5. Török B., Felföldi K., Balázsik K., Bartók M. Chem. Commun. 1999;1725.
6. Huck W.-R., Mallat T., Baiker A. J. Catal. 193:2000;1.
7. Wells P.B., Simons K.E., Slipszenko J.A., Griffiths S.P., Ewing D.F. J. Mol. Catal. A. 146:1999;159.
8. Minder B., Mallat T., Baiker A., Wang G., Heinz T., Pfaltz A. J. Catal. 154:1995;317.
9. Tungler A., Mátheé T., Tarnai T., Fodor K., Tóth G., Kajtár J., Kolossváry I., Herényi B., Sheldon R.A. Tetrahedron Assym. 6:1995;2395.
10. M.J. Stephenson, R.M. Lambert, J. Phys. Chem. B, submitted for publication.
11. Lorenzo M.O., Baddeley C.J., Muryn C., Raval R. Nature. 23:2000;376.
12. Lorenzo M.O., Haq S., Bertrams T., Murray P., Raval R., Baddeley C.J. J. Phys. Chem. B. 103:1999;10661.
13. Hoek A., Sachtler W.M.H. J. Catal. 58:1979;276.
14. Keane M.A., Webb G. J. Catal. 136:1992;1.
15. Raval R. Cattech. 5:2001;12.
16. Giancarlo L.C., Flynn G.W. Acc. Chem. Res. 33:2000;491.
17. McFadden C.F., Cremer P.S., Gellman A.J. Langmuir. 12:1996;2483.
18. Ahmadi A., Attard G., Feliu J., Rodes A. Langmuir. 15:1999;2420.
19. Attard G.A. J. Phys. Chem. B. 105:2001;3158.
20. Besson M., Delbecq F., Gallezot P., Neto S., Pinel C. Chem. Eur. J. 6:2000;949.
21. S. Neto, Hydrogénation diastéréosélective de composés aromatiques disubstiués sur des catalyseurs métalliques supportés, PhD thesis, Université Claude Bernard-Lyon 1, 1998.
22. Besson M., Blanc B., Champelet M., Gallezot P., Nasar K., Pinel C. J. Catal. 170:1997;254.
23. Kresse G., Furthmüller J. Comp. Mat. Sci. 16:1996;15.
24. Kresse G., Furthmüller J. Phys. Rev. B. 54:1996;169.
25. Perdew J., Zunger A. Phys. Rev. B. 23:1981;8054.
26. Perdew J., Wang Y. Phys. Rev. B. 33:1986;8800.
27. Vanderbilt D. Phys. Rev. B. 41:1990;7892.
28. Kresse G., Hafner J. J. Phys. Condens. Matter. 6:1994;8245.
29. Loffreda D., Simon D., Sautet P. Chem. Phys. Lett. 291:1998;15.
30. Kittel C. Introduction to Solid State Physics. 1996;Wiley, Chichester. Chap. 1.
31. Lin R.F., Blackmann G.S., van Hove M.A., Somorjai G.A. Acta Crystallogr. B. 43:1987;368.
32. Mittendorfer F., Hafner J. Surf. Sci. 472:2001;133.
33. N. Douja, Synthèse asymétrique de pipéridines par hydrogénation diastéréosélective de dérivés nicotiniques sur des catalyseurs métalliques supportés, PhD thesis, Université Claude Bernard-Lyon 1, 2001.
34. Prasad K.H.V., Prasad K.B.S., Mallikarjunan M.M., Vaidyeswaram M. J. Catal. 84:1983;65.
35. Lee I.C., Masel R.I. J. Phys. Chem. B. 106:2002;368.
36. Lee J.-G., Ahner J., Yates J.T. Jr. J. Chem. Phys. 114:2001;1414.
37. Wan L.-J., Wang C., Bai C.-L., Osawa M. J. Phys. Chem. B. 105:2001;8399.
38. Frechard F., van Santen R.A., Siokou A., Niemantsverdriet J.W. J. Chem. Phys. 111:1999;8124.
39. Roberts J.D., Caserio M.C. Basic principles of Organic Chemistry. 1965;Benjamin, New York.
40. N. Douja, M. Besson, P. Gallezot, C. Pinel, J. Mol. Catal., submitted for publication.