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 jul 2016
Accepted
03 okt 2016
First published
03 okt 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements