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Synthesis of N-heterocycles from diamines via H2-driven NADPH recycling in the presence of O2

Al-Shameri, Ammar; Borlinghaus, Niels; Weinmann, Leonie; Scheller, Philipp N.; Nestl, Bettina M.; Lauterbach, Lars

Herein, we report an enzymatic cascade involving an oxidase, an imine reductase and a hydrogenase for the H2-driven synthesis of N-heterocycles. Variants of putrescine oxidase from Rhodococcus erythropolis with improved activity were identified. Substituted pyrrolidines and piperidines were obtained with up to 97% product formation in a one-pot reaction directly from the corresponding diamine substrates. The formation of up to 93% ee gave insights into the specificity and selectivity of the putrescine oxidase.
Published in: Green Chemistry, 10.1039/C8GC03798A, Royal Society of Chemistry