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For a detailed analysis illustrated with many examples including the use of enzymes, see reference [2].
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A. Collet, Angew. Chem. 1998, 110, 3429; Angew. Chem. Int. Ed. 1998, 37, 3239.
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Broxterman, Q.M.7
Minnaard, A.8
Kaptein, B.9
Van Der Sluis, S.10
Hulshof, L.11
Kooistra, J.12
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T. Vries, H. Wynberg, E. van Echten, J. I Koek, W. ten Hoeve, R. M. Kellogg, Q. M. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, J. Kooistra, Angew. Chem. 1998, 110, 2491; Angew. Chem. Int. Ed. 1998, 37, 2349.
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O. Dapremont, F. Geiser, T. Zhang, S. S. Guhan, R. M. Guinn, G. J. Quallich, US Pat. 6444854, 2002.
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4544336675
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Note
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In favorable cases, the benefits of continuous chromatography outweigh the capital expense for specialty equipment, which can be operated internally or at a specialist company.
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11
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0038384673
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Stoichiometric chiral ligands (chiral mediators) do not require attachment and cleavage steps and in an optimized case can be recycled in the same reaction vessel by in situ regeneration of the active species: A. Choudhury, J. R. Moore, M. E. Pierce, J. M. Fortunak, I. Valvis, P. N. Confalone, Org. Process Res. Dev. 2003, 7, 324.
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A. Piscopio, J. M. Hawkins, S. Caron, S. E. Kelly, J. W. Raggon, M. J. Castaldi, R. W. Dugger, S. G. Ruggeri, US. Pat 6096906, 2000.
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Dugger, R.W.7
Ruggeri, S.G.8
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0028059105
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For other multistep routes to sertraline tetralone (S)-1 by using asymmetric catalysis, see: E. J. Corey, T. G. Gant, Tetrahedron Lett. 1994, 35, 5373; M. Lautens, T. Rovis, J. Org. Chem. 1997, 62, 5246; H. M. L. Davies, D. G. Stafford, T. Hansen, Org. Lett. 1999, 1, 233.
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For other multistep routes to sertraline tetralone (S)-1 by using asymmetric catalysis, see: E. J. Corey, T. G. Gant, Tetrahedron Lett. 1994, 35, 5373; M. Lautens, T. Rovis, J. Org. Chem. 1997, 62, 5246; H. M. L. Davies, D. G. Stafford, T. Hansen, Org. Lett. 1999, 1, 233.
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For other multistep routes to sertraline tetralone (S)-1 by using asymmetric catalysis, see: E. J. Corey, T. G. Gant, Tetrahedron Lett. 1994, 35, 5373; M. Lautens, T. Rovis, J. Org. Chem. 1997, 62, 5246; H. M. L. Davies, D. G. Stafford, T. Hansen, Org. Lett. 1999, 1, 233.
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PCT Int. Appl. WO 9502585, 1995
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G. J. Quallich, PCT Int. Appl. WO 9502585, 1995.
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4544344401
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April
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Thommen, M.1
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33751157286
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For example, the scarce supply and expense of binap prompted Merck chemists to develop a simple and efficient synthesis of binap: D. Cai, J. E Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 7180.
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Verhoeven, T.R.5
Reider, P.J.6
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23
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4544388670
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Palladium prices from http://www.kitco.com/charts/historicalpalladium. html. We thank Dr. Don Zeng of Heraeus for pointing out this internet reference.
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24
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0033548571
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27
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4544372878
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Note
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Crystallization of the product of an asymmetric catalytic reaction, a step often included to enhance the optical purity, can contribute to the robustness of the process (for example, in the case of varying selectivity), provided that the optical purity does not drop below the eutectic composition.
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