Journal of the American Chemical Society, Vol.141, No.49, 19208-19213, 2019
One-Pot Biocatalytic Cascade Reduction of Cyclic Enimines for the Preparation of Diastereomerically Enriched N-Heterocycles
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 (alpha,beta-unsaturated imines). Preliminary studies suggest their hydrolyzed ring-open ?omega-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.