One-Pot Biocatalytic Cascade Reduction of Cyclic Enimines for the Preparation of Diastereomerically Enriched N-Heterocycles

J Am Chem Soc. 2019 Dec 11;141(49):19208-19213. doi: 10.1021/jacs.9b10053. Epub 2019 Nov 26.

Abstract

Ene-reductases (EREDs) catalyze the reduction of electron-deficient C═C bonds. Herein, we report the first example of ERED-catalyzed net reduction of C═C bonds of enimines (α,β-unsaturated imines). Preliminary studies suggest their hydrolyzed ring-open ω-amino enones are the likely substrates for this step. When combined with imine reductase (IRED)-mediated C═N reduction, the result is an efficient telescoped sequence for the preparation of diastereomerically enriched 2-substituted saturated amine heterocycles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Imines / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Oxidoreductases / chemistry*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Imines
  • Oxidoreductases