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

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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

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Article information

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

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

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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

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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

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

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