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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 |
