Issue 2, 2017

Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases

Abstract

A one-pot/two-step bienzymatic asymmetric amination of secondary alcohols is disclosed. The approach is based on a sequential strategy involving the use of a laccase/TEMPO catalytic system for the oxidation of alcohols into ketone intermediates, and their following transformation into optically enriched amines by using transaminases. Individual optimizations of the oxidation and biotransamination reactions have been carried out, studying later their applicability in a concurrent process. Therefore, 17 racemic (hetero)aromatic sec-alcohols with different substitutions in the aromatic ring have been converted into enantioenriched amines with good to excellent selectivities (90–99% ee) and conversion values (67–99%). The scalability of the process was also demonstrated when two different amine donors were used in the transamination step, such as isopropylamine and cis-2-buten-1,4-diamine. Satisfyingly, both sacrificial amine donors can shift the equilibrium toward the amine formation, leading to the corresponding isolated enantioenriched amines with good to excellent results.

Graphical abstract: Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases

Supplementary files

Article information

Article type
Paper
Submitted
20 7 2016
Accepted
03 10 2016
First published
03 10 2016

Green Chem., 2017,19, 474-480

Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases

L. Martínez-Montero, V. Gotor, V. Gotor-Fernández and I. Lavandera, Green Chem., 2017, 19, 474 DOI: 10.1039/C6GC01981A

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