Abstract
Enantioselective heterogeneous catalysis is an important and rapidly expanding research area. The two most heavily researched examples of this type of catalysis are the enantioselective hydrogenation of α-ketoesters over Pt-based catalysts and the enantioselective hydrogenation of β-ketoesters over Ni-based catalysts. These systems share one extremely important common feature—the enantioselective surface reaction is controlled by the presence of adsorbed chiral molecules (modifiers) on the surface of the metal component of the catalyst. In each system, a number of models have been proposed to explain the enantioselective behavior in the light of catalytic experiments. In recent years, surface science has begun to address the issues relevant to this branch of catalysis. This article reviews to what extent surface science has enabled the verification of the proposed models and, in addition, what new light surface science has shed on the possible mechanisms of enantioselective heterogeneous catalysis.
Similar content being viewed by others
References
B. Sharpless, W. Knowles and R. Noyori, Chem. Br. 37 (2001) 24.
G. Webb and P.B. Wells, Catal. Today 12 (1992) 319.
Y. Izumi, Adv. Catal. 32 (1983) 215.
A. Tai and T. Harada, in Tailored Metal Catalysts, Y. Isawawa (ed.) (D. Reidel Publishing Company, 1986) pp. 265-324.
A. Tai and T. Sugimura, in Chiral Catalyst Immobilisation and Recycling, Chapter 8, D.E. de Vos, I.F.J. Vankelecom and P.A. Jacobs (eds.) (Wiley-VCH, 2000) pp. 173-208.
Y. Orito, S. Imai and S. Niwa, Nippon Kagaku Kaishi (1979) 1118.
I.M. Sutherland, A. Ibbotson, R.B. Moyes and P.B. Wells, J. Catal. 125 (1990) 77.
J.L. Gland and G.A. Somorjai, Surf. Sci. 38 (1973) 157.
A. Hoek and W.M.H. Sachtler, J. Catal. 58 (1979) 276.
M.A. Keane, Langmuir 13 (1997) 41.
K. Ito, T. Harada, A. Tai and Y. Izumi, Chem. Lett. (1979) 1049.
I. Yasumori, Pure Appl. Chem. 50 (1978) 971.
Y.I. Petrov and E.I. Klabunovskii, Kinet. Catal. 8 (1967) 814.
J.A. Groenewegen and W.M.H. Sachtler, Proc. 6th Int. Congress on Catalysis (London, 1976) 1014.
A.F. Carley, M.K. Rajumon, M.W. Roberts and P.B. Wells, J. Chem. Soc., Faraday Trans. 91 (1995) 2167.
J.M. Bonello, F.J. Williams and R.M. Lambert, J. Am. Chem. Soc. 125 (2003) 2723.
T. Heinz, G. Wang, A. Pfaltz, A. Minder, M. Schurch, T. Mallat and A. Baiker, J. Chem. Soc. Chem. Commun. (1995) 1421.
A. Minder, M. Schurch, T. Mallat, A. Baiker, T. Heinz and A. Pfaltz, J. Catal. 160 (1996) 261.
J.M. Bonello and R.M. Lambert, Surf. Sci. 498 (2002) 212.
S. Haq and D.A. King, J. Phys. Chem. 100 (1996) 16957.
J.M. Bonello, E.C.H. Sykes, R. Lindsay, F.J. Williams, A.K. Santra and R.M. Lambert, Surf. Sci. 482-485 (2001) 207.
T. Evans, A.P. Woodhead, A. Gutierrez-Sosa, G. Thornton, T.J. Hall, A.A. Davis, N.A. Young, P.B. Wells, R.J. Oldman, O. Plaskevych, O. Vahtras, H. Agren and V. Carravetta, Surf. Sci. 436 (1999) L691.
M. Ortega Lorenzo, S. Haq, T. Bertrams, P.W. Murray, R. Raval and C.J. Baddeley, J. Phys. Chem. B 103 (1999) 10661.
M.O. Lorenzo, V. Humblot, P. Murray, C.J. Baddeley, S. Haq and R. Raval, J. Catal. 205 (2002) 123.
M.O. Lorenzo, C.J. Baddeley, C. Muryn and R. Raval, Nature 404 (2000) 376.
R. Raval, C.J. Baddeley, S. Haq, S. Louafi, P. Murray, C. Muryn, M.O. Lorenzo and J. Williams, Stud. Surf. Sci. Catal. 122 (1999) 11.
L.A.M.M. Barbosa and P. Sautet, J. Am. Chem. Soc. 123 (2001) 6639.
T.E. Jones and C.J. Baddeley, Surf. Sci. 513 (2002) 453.
V. Humblot, S. Haq, C. Muryn, W. Hofer and R. Raval, J. Am. Chem. Soc. 124 (2002) 503.
T.E. Jones and C.J. Baddeley, in preparation.
J.D. Horvath and A.J. Gellman, J. Am. Chem. Soc. 124 (2002) 2384.
J.D. Horvath and A.J. Gellman, J. Am. Chem. Soc. 123 (2001) 7953.
C.F. McFadden, P.S. Cremer and A.J. Gellman, Langmuir 12 (1996) 2483.
G.A. Attard, J. Phys. Chem. B 105 (2001) 3158.
G.A. Attard, J.E. Gillies, C.A. Harris, D.J. Jenkins, P. Johnston, M.A. Price, D.J. Watson and P.B. Wells, Appl. Catal. A: Gen. 222 (2001) 393.
M.J. Stephenson and R.M. Lambert, J. Phys. Chem. B 105 (2001) 12832.
G.A. Attard, C. Harris, E. Herrero and J. Feliu, Faraday Disc. 121 (2002) 253.
Q. Chen, D.J. Frankel and N.V. Richardson, Langmuir 17 (2001) 8276.
X.Y. Zhao, J. Am. Chem. Soc. 122 (2000) 12584.
T.E. Jones, A.J. Urquhart and C.J. Baddeley, in preparation.
J.M. Bonello, E.C.H. Sykes, R. Lindsay, F.J. Williams, A.K. Santra and R.M. Lambert, Surf. Sci. 482-485 (2001) 207.
J.M. Bonello, F.J. Williams, A.K. Santra and R.M. Lambert, J. Phys. Chem. B 104 (2000) 9696.
J.M. Bonello, R.M. Lambert, N. Kunzle and A. Baiker, J. Am. Chem. Soc. 122 (2000) 9864.
J.M. Bonello, F.J. Williams and R.M. Lambert, J. Am. Chem. Soc. 125 (2003) 2723.
T.E. Jones and C.J. Baddeley, Surf. Sci. 519 (2002) 237.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Baddeley, C. Fundamental Investigations of Enantioselective Heterogeneous Catalysis. Topics in Catalysis 25, 17–28 (2003). https://doi.org/10.1023/B:TOCA.0000003095.06727.39
Issue Date:
DOI: https://doi.org/10.1023/B:TOCA.0000003095.06727.39