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 Black; Nicola Brown; Nicholas J. Turner; Renzo Luisi; Daniele Castagnolo

doi:10.1039/c9ob01962f

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 Black, Nicola Brown, Nicholas J. Turner, Renzo Luisi, Daniele Castagnolo^*

^*Corresponding author for this work

Applied Sciences Department

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English
Pages (from-to)	8982-8986
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	40
Early online date	25 Sept 2019
DOIs	https://doi.org/10.1039/c9ob01962f
Publication status	Published - 28 Oct 2019

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

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.",

author = "Kate Lauder and Domiziana Masci and Anita Toscani and {Al Mekdad}, Aya and Gary Black and Nicola Brown and Turner, {Nicholas J.} and Renzo Luisi and Daniele Castagnolo",

year = "2019",

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doi = "10.1039/c9ob01962f",

language = "English",

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publisher = "Royal Society of Chemistry",

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Lauder, K, Masci, D, Toscani, A, Al Mekdad, A, Black, G , Brown, N, Turner, NJ, Luisi, R & Castagnolo, D 2019, 'A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution', Organic and Biomolecular Chemistry, vol. 17, no. 40, pp. 8982-8986. https://doi.org/10.1039/c9ob01962f

TY - JOUR

T1 - A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution

AU - Lauder, Kate

AU - Masci, Domiziana

AU - Toscani, Anita

AU - Al Mekdad, Aya

AU - Black, Gary

AU - Brown, Nicola

AU - Turner, Nicholas J.

AU - Luisi, Renzo

AU - Castagnolo, Daniele

PY - 2019/10/28

Y1 - 2019/10/28

N2 - 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.

AB - 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.

U2 - 10.1039/c9ob01962f

DO - 10.1039/c9ob01962f

M3 - Article

C2 - 31584061

AN - SCOPUS:85073488621

SN - 1477-0520

VL - 17

SP - 8982

EP - 8986

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 40

ER -

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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