By Blaser H.U., Schmidt E. (eds.)
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Additional resources for Asymmetric Catalysis on Industrial Scale.. Challenges, Approaches and Solutions
1: Chiral Ligands for Asymmetric Catalysis. 6 M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1993, 115, 10125; M. J. Burk, M. F. Gross, J. P. Martinez, J. Am. Chem. Soc. 1995, 117, 9375. 7 J. Halpern in Asymmetric Synthesis, Vol. 5, Chiral Catalysis (J. D. ), Academic Press, New York, 1985, chap. 2: Asymmetric Catalytic Hydrogenation: Mechanism and Origin of Enantioselection. 39 2 The Other L-Dopa Process Rçdiger Selke Abstract In January 1986 Isicom, a prescription drug used to treat the Parkinson syndrome, went on sale in the former German Democratic Republic.
Early on we tried phosphanes with a chiral alkyl side chain, and the asymmetric bias was barely detectable. We felt strongly that, if one wanted to obtain high ee values, the asymmetry would have to be directly on the phosphorus. That is where the action is. Initially, we varied the alkyl groups on the phosphorus, by converting the normal propyl to the more hindered isopropyl or cyclohexyl, but ee values still re- 25 26 1 Asymmetric Hydrogenations ± The Monsanto L-Dopa Process Fig. 2 The Hoffman-LaRoche l-dopa process.
This should provide some steric hindrance as well as a possible hydrogen-bonding site. Furthermore, the ether linkage would be stable enough to survive the rigors of a phosphane synthesis. In those days, our small group was in constant contact and what we decided to do was arrived at by informal consensus. I hate to admit it, but it is much easier to invent when working in a small, underfunded group. Being lean and hungry is conducive to invention. We prepared methylphenyl-o-anisylphosphane (PAMP) and obtained ee values, after playing with the hydrogenation conditions, of up to 58%.
Asymmetric Catalysis on Industrial Scale.. Challenges, Approaches and Solutions by Blaser H.U., Schmidt E. (eds.)