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

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Abstract

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.

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

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Publication details

The article was received on 05 Dec 2018, accepted on 23 Jan 2019 and first published on 23 Jan 2019


Article type: Communication
DOI: 10.1039/C8GC03798A
Citation: Green Chem., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Synthesis of N-heterocycles from diamines via H2-driven NADPH recycling in the presence of O2

    A. Al-Shameri, N. Borlinghaus, L. Weinmann, P. N. Scheller, B. M. Nestl and L. Lauterbach, Green Chem., 2019, Advance Article , DOI: 10.1039/C8GC03798A

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