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 (α,β-unsaturated imines). Preliminary studies suggest their hydrolyzed ring-open ω-amino enones are the likely substrates for th...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-12, Vol.141 (49), p.19208-19213
Main Authors: Thorpe, Thomas W, France, Scott P, Hussain, Shahed, Marshall, James R, Zawodny, Wojciech, Mangas-Sanchez, Juan, Montgomery, Sarah L, Howard, Roger M, Daniels, David S. B, Kumar, Rajesh, Parmeggiani, Fabio, Turner, Nicholas J
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b10053