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2). This enamide offered a golden opportunity for commercializing this burgeoning technology. We soon found out that these prochiral enamide precursors of a-amino acids hydrogenated much faster than one would expect for such a highly substituted olefin. Even so, the chiral results were only 28%, but the stage was then nicely set to carry out a structure versus activity study. We had a good test reaction, as shown in Fig. 3, in which we used the simple phenylalanine intermediate. We also had a good test for efficiency, since all we had to do was run rotation measurements on an appropriately diluted reaction mixture.
Pettman, Specialty Chemicals, 1994, 12. B. D. Hewitt, Pharmacia & Upjohn, Chem. Eng. News, 1 November 1999, p. 35. 9 References 24 25 26 27 28 29 R. A. Holt, Chim. Oggi 1996, 14, 17. T. Aratani in Comprehensive Asymmetric Catalysis (E. N. Jacobsen, H. Yamamoto, A. ), Springer, Berlin, 1999, p. 1451. T. Aratani, Pure Appl. Chem. 1985, 57, 1839. R. Schmid, M. N. Jacobsen, H. Yamamoto, A. ), Springer, Berlin, 1999, p. 1439. a) R. Schmid, E. A. Broger, Proceedings of the ChiralEurope '94 Symposium, Spring Innovation, Stockport, UK, 1994, p.
P. 349). It is important to realize that the effectiveness of the catalytic step is only one, albeit often an important, factor but that it is the cost of the overall synthesis which is decisive for the final choice as to which route will be chosen. The comparison of competing routes is not always easy and different approaches can be found in the contributions of Blaser et al. (p. 91), Pesti and Anzalone (p. 365), or Singh et al. (p. 335). In some cases, the overall synthesis is actually designed around an effective enantioselective transformation as for example described for the metolachlor process by Blaser et al.