Deracemization By Simultaneous Bio-oxidative Kinetic Resolution and Stereoinversion**

نویسندگان

  • Joerg 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
چکیده

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.

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عنوان ژورنال:

دوره 53  شماره 

صفحات  -

تاریخ انتشار 2014