Deracemization by Simultaneous Bio-oxidative Kinetic Resolution and Stereoinversion

Jörg H. Schrittwieser, Bas Groenendaal, Verena Resch, Diego Ghislieri, Silvia Wallner, Eva-Maria Fischereder, Elisabeth Fuchs, Barbara Grischek, Johann H. Sattler, Peter Macheroux, Nicholas J. Turner*, Wolfgang Kroutil*

*Korrespondierende/r Autor/-in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikelBegutachtung

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.
Originalspracheenglisch
Seiten (von - bis)3731-3734
FachzeitschriftAngewandte Chemie - International Edition
Jahrgang53
Ausgabenummer14
DOIs
PublikationsstatusVeröffentlicht - 2014

Fields of Expertise

  • Human- & Biotechnology

Treatment code (Nähere Zuordnung)

  • Basic - Fundamental (Grundlagenforschung)

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