Abstract
During the last two decades an increasing number of catalytic, enantioselective reactions have been developed.1 Life science companies, which increasingly demand the preparation of enantiomerically pure products on large scale, have also fuelled the development of such methodologies with an emphasis on manufacturability.2 Asymmetric hydrogenations of prochiral C=C, C=O and C=N double bonds, catalysed by chiral transition metal complexes are highly attractive and continue to be an efficient method for generating stereogenic centres in an enantioselective fashion.1c Critical factors which determine the outcome of an enantioselective hydrogenation on large scale are outlined in Figure 1. The chemistry of specific examples from LONZA’s own experience with this technology is presented in this report.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
I. Ojima. Catalytic Asymmetric Synthesis, VCH Publishers Inc., New York (1993).
D.J. Ager, M.B. East. Asymmetric Synthetic Methodology, CRC Press, Inc., Boca Raton (1996).
R. Noyori. Asymmetric Catalysis in Organic Chemistry, New York (1994).
I.W. Davis, P.J. Reider, Practical asymmetric synthesis, Chemistry and Industry 3 June: 412(1996).
P.J. De Clercq, Biotin: a timeless challenge for total synthesis, Chem. Rev. 97: 1755 (1997).
T. Meul, R. Miller, L. Tenud, Ökonomische Herstellung von Feinchemikalien: Tetronsäure, Chimia 41: 73 (1987).
J. Mc Garrity, L. Tenud, EP Appl. EP 273 270; CA 110: 75 168j (1988).
M. Eyer, R. Fuchs,, J. Mc Garrity, EP Appl. EP 602 653; CA 121: 230 774b (1994).
M. Eyer, R.E. Merrill, PCT Int. Appl. WO 94 24 137; CA 122: 56 043w (1994).
J. Mc Garrity, F. Spindler, R. Fuchs, M. Eyer, EP Appl. EP 624 587; CA 122: 81 369q(1994).
W. Brieden, Taking the right route to the manufacture of enantiomerically pure fine chemicals, Proceedings of the Chiral USA’ 97 Symposium, p. 45.
E. Felder, S. Maffei, S. Pietra, D. Pitré, Über die katalytische Hydrierung von Pyrazincarbonsäuren, Helv. Chim. Acta 43: 888 (1960).
K. Rossen, S.A. Weissman, J. Sager, D. Askin, R.P. Volante, P.J. Reider, Asymmetric hydrogenation of tetrahydropyrazines: synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor Indinavir, Tetrahedron Lett. 36: 6419 (1995).
R. Fuchs, EP Appl. EP 803 502; CA 128: 13 286 (1997).
D.C. Muchmore, US Patent 5 215 918 (1993).
W. Brieden, EP Appl. EP 785 198; CA 127: 176 346 (1997).
M. Kitamura, Y. Hsiao, M. Ohta, M. Tsukamoto, T. Ohta, H. Takaya, R. Noyori, General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-Ruthenium(II) complexes, J. Org. Chem. 59: 297(1994).
B. Heiser, E.A. Broger, Y. Crameri, New efficient methods for the synthesis and in-situ preparation of Ruthenium(II) complexes of atropisomeric diphosphines and their application in asymmetric catalytic hydrogenations, Tetrahedron: Asymmetry 2: 51 (1991).
O. Werbitzky, PCT Int. Appl. WO 97 03 052 (1997).
O. Werbitzky, Technical synthesis of a morphine alkaloid through an enantioselective hydrogenation of a cyclic imine, Proceedings of the Chiral Europe’ 97 Symposium, p. 37.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Science+Business Media New York
About this chapter
Cite this chapter
Brieden, W. (1999). Large Scale Catalytic Asymmetric Hydrogenation, an Industrial Perspective. In: Scolastico, C., Nicotra, F. (eds) Current Trends in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4801-0_20
Download citation
DOI: https://doi.org/10.1007/978-1-4615-4801-0_20
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-7175-5
Online ISBN: 978-1-4615-4801-0
eBook Packages: Springer Book Archive