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Deracemization By Simultaneous Bio‐oxidative Kinetic Resolution and Stereoinversion |
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| Authors: | Dr. Joerg H. Schrittwieser Dr. Bas Groenendaal Dr. Verena Resch Dr. Diego Ghislieri Dr. Silvia Wallner Eva‐Maria Fischereder Elisabeth Fuchs Barbara Grischek Dr. Johann H. Sattler Prof. Dr. Peter Macheroux Prof. Dr. Nicholas J. Turner Prof. Dr. Wolfgang Kroutil |
| Affiliation: | 1. Institut für Chemie, Organische und Bioorganische Chemie, Karl‐Franzens‐Universit?t Graz, Heinrichstrasse 28, A‐8010 Graz (Austria);2. School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester, M1 7DN (UK);3. Institut für Biochemie, Technische Universit?t Graz, Petersgasse 12, 8010 Graz (Austria) |
| Abstract: | Deracemization, that is, the transformation of a racemate into a single product enantiomer with theoretically 100 % conversion and 100 % ee, is an appealing but also challenging option for asymmetric synthesis. Herein a novel chemo‐enzymatic deracemization concept by a cascade is described: the pathway involves two enantioselective oxidation steps and one non‐stereoselective reduction step, enabling stereoinversion and a simultaneous kinetic resolution. The concept was exemplified for the transformation of rac‐benzylisoquinolines to optically pure (S)‐berbines. The racemic substrates were transformed to optically pure products (ee>97 %) with up to 98 % conversion and up to 88 % yield of isolated product. |
| Keywords: | alkaloids asymmetric synthesis C C coupling deracemization enzyme catalysis simultaneous cascades |