Issue 6, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Dec 2018
Accepted
23 Jan 2019
First published
23 Jan 2019
This article is Open Access
Creative Commons BY license

Green Chem., 2019,21, 1396-1400

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, 21, 1396 DOI: 10.1039/C8GC03798A

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