Deracemization By Simultaneous Bio‐oxidative Kinetic Resolution and Stereoinversion1. Issue 14 (24th February 2014)

• Record Type: Journal Article
• Authors: Schrittwieser, Joerg H.; Groenendaal, Bas; Resch, Verena; Ghislieri, Diego; Wallner, Silvia; Fischereder, Eva‐Maria; Fuchs, Elisabeth; Grischek, Barbara; Sattler, Johann H.; Macheroux, Peter; Turner, Nicholas J.; Kroutil, Wolfgang
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 14(2014)
• Page Start: 3731
• Page End: 3734
• Publication Date: 2014-02-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201400027
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Deracemization, that is, the transformation of a racemate into a single product enantiomer with theoretically 100 % conversion and 100 % <italic>ee</italic>, 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 <italic>rac</italic>‐benzylisoquinolines to optically pure (<italic>S</italic>)‐berbines. The racemic substrates were transformed to optically pure products (<italic>ee</italic>&gt;97 %) with up to 98 % conversion and up to 88 % yield of isolated product.</p> </abstract>