Hydrogenation of butane-2,3-dione with heterogeneous cinchona modified platinum catalysts: a combination of an enantioselective reaction and kinetic resolution

Abstract

(R)-3-Hydroxybutan-2-one was obtained with 85–90% ee albeit in low yield by the Pt/Al₂O₃ cinchona catalyzed hydrogenation of butane-2,3-dione by a combination of enantioselective hydrogenation and kinetic resolution.

References

1. H. U. Blaser, H. P. Jalett, M. Müller and M. Studer, Catal. Today, 1997, 37, 441.
2. S. Nakagawa, T. Sugimura and A. Tai, Chem. Lett., 1997, 589.
3. A. Tai, K. Ito and T. Harada, Bull. Chem. Soc. Jpn., 1981, 54, 223.
4. A. Tai, T. Kikukawa, T. Sugimura, Y. Inoue, S. Abe, T. Osawa, S. Fujii and T. Harada, Bull. Chem. Soc. Jpn., 1994, 67, 2473.
5. H. U. Blaser, H. P. Jalett and J. Wiehl, J. Mol. Catal., 1991, 68, 215.
6. W. A. H. Vermeer, A. Fulford, P. Johnston and P. B. Wells, J. Chem. Soc., Chem. Commun., 1993, 1053.
7. T. Mallat, M. Bodmer and A. Baiker, Catal. Lett., 1997, 44, 95.
8. G. Z. Wang, T. Mallat and A. Baiker, Tetrahedron: Asymmetry, 1997, 8, 2133.
9. V. Okafor, H.-U. Blaser and M. Studer, unpublished results.
10. M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya and R. Noyori, J. Am. Chem. Soc., 1988, 110, 629.
11. Q.-h. Fan, C.-h. Yeung and A. S. C. Chan, Tetrahedron: Asymmetry, 1997, 8, 4041.
12. H. Brunner, T. Amberger and J. Wiehl, Bull. Soc. Chem. Belg., 1991, 100, 571.