Abstract

The influence of pH on the asymmetric hydrogenation of α-amino acid precursors was investigated in the presence of different types of amphiphiles in water as medium. Non-ionic, cationic and zwitterionic amphiphiles gave optimal results with respect to activity and enantioselectivity between pH 2 and pH 5. Anionic amphiphiles were effective in the range from pH 2 up to pH 8 (sometimes pH 9). Comparable results were obtained with cationic and anionic polymeric micelles. Some relationships exist between CH/CD exchange in D2O and the pH dependence of the hydrogenation. As a practical consequence the pH in micellar hydrogenation systems should be chosen between pH 2 and pH 4.

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