Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion.

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.

SUBMITTER: Schrittwieser JH 

PROVIDER: S-EPMC4499246 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature