A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution

Kate Lauder; Domiziana Masci; Anita Toscani; Aya Al Mekdad; Gary W. Black; Nicola L. Brown; Nicholas J. Turner; Renzo Luisi; Daniele Castagnolo

doi:10.1039/C9OB01962F

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution†

Kate Lauder,

^a Domiziana Masci,^a Anita Toscani,^a Aya Al Mekdad,^a Gary W. Black,

^b Nicola L. Brown,^b Nicholas J. Turner,

^c Renzo Luisi

^d and Daniele Castagnolo

*^a

Author affiliations

* Corresponding authors

^a School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, London, UK
E-mail: daniele.castagnolo@kcl.ac.uk

^b Department of Applied Sciences, Northumbria University, Ellison Place, Newcastle upon Tyne, UK

^c School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester, UK

^d Department of Pharmacy - Drug Sciences, University of Bari“A. Moro”, Via E. Orabona 4, Bari 70125, Italy

Abstract

A facile microwave assisted three-component protocol allows the synthesis of chiral aryl-1,2-mercaptoamines in water in a few minutes with high yields, bypassing the use of toxic aziridine intermediates. The chiral 1,2-mercaptoamines were then deracemized through enzymatic resolution of the racemates using monoamine oxidase (MAO-N) biocatalysts.

This article is part of the themed collections: Sustainable synthesis and catalysis – Chemical Science symposium collection and Synthetic methodology in OBC

Download options Please wait...

Supplementary files

Supplementary information PDF (1159K)

Article information

DOI: https://doi.org/10.1039/C9OB01962F
Article type: Communication
Submitted: 07 sep. 2019
Accepted: 25 sep. 2019
First published: 25 sep. 2019

Download Citation

Org. Biomol. Chem., 2019,17, 8982-8986

Permissions

Request permissions

A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution

K. Lauder, D. Masci, A. Toscani, A. Al Mekdad, G. W. Black, N. L. Brown, N. J. Turner, R. Luisi and D. Castagnolo, Org. Biomol. Chem., 2019, 17, 8982 DOI: 10.1039/C9OB01962F

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.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution†

Abstract

Supplementary files

Article information

Download Citation

Permissions

A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution

Social activity

Search articles by author

Spotlight

Advertisements