Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion

Research output: Contribution to journalArticle

  • External authors:
  • Joerg Schrittwieser
  • Bas Groenendaal
  • V Resch
  • Diego Ghislieri
  • S. Wallner
  • E-M. Fischereder
  • E. Fuchs
  • B. Grischek
  • J.H. Sattler
  • P Macheroux
  • Wolfgang Kroutil

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.

Bibliographical metadata

Original languageEnglish
Pages (from-to)3731-3734
JournalAngewandte Chemie - International Edition
Volume53
Issue number14
DOIs
StatePublished - 2014