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

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^*

^*Autore corrispondente per questo lavoro

King's College London
Northumbria University
University of Manchester
University of Bari

Risultato della ricerca: Contributo in rivista › Articolo › peer review

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.

Lingua originale	Inglese
pagine (da-a)	8982-8986
Numero di pagine	5
Rivista	ORGANIC & BIOMOLECULAR CHEMISTRY
Volume	17
DOI	https://doi.org/10.1039/c9ob01962f
Stato di pubblicazione	Pubblicato - 2019

Keywords

Aryl-1,2-mercaptoamines
Chirality
Green approach
Monoamine oxidase biocatalysts
One-pot microwave-mediated synthesis
Water

Accesso al documento

10.1039/c9ob01962f

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Lauder, K., Masci, D., Toscani, A., Al Mekdad, A., Black, G. W., Brown, N. L., Turner, N. J., 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 & BIOMOLECULAR CHEMISTRY, 17, 8982-8986. https://doi.org/10.1039/c9ob01962f

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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.",

keywords = "Aryl-1,2-mercaptoamines, Chirality, Green approach, Monoamine oxidase biocatalysts, One-pot microwave-mediated synthesis, Water, Aryl-1,2-mercaptoamines, Chirality, Green approach, Monoamine oxidase biocatalysts, One-pot microwave-mediated synthesis, Water",

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

year = "2019",

doi = "10.1039/c9ob01962f",

language = "English",

volume = "17",

pages = "8982--8986",

journal = "ORGANIC \& BIOMOLECULAR CHEMISTRY",

issn = "1477-0520",

publisher = "Royal Society of Chemistry:Thomas Graham House, Science Park, Cambridge CB4 0WF United Kingdom:011 44 1223 432360, EMAIL: [email protected], INTERNET: http://www.rsc.org, http://www.chensoc.org, Fax: 011 44 1223 423429",

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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 W.

AU - Brown, Nicola L.

AU - Turner, Nicholas J.

AU - Luisi, Renzo

AU - Castagnolo, Daniele

PY - 2019

Y1 - 2019

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.

KW - Aryl-1,2-mercaptoamines

KW - Chirality

KW - Green approach

KW - Monoamine oxidase biocatalysts

KW - One-pot microwave-mediated synthesis

KW - Water

KW - Aryl-1,2-mercaptoamines

KW - Chirality

KW - Green approach

KW - Monoamine oxidase biocatalysts

KW - One-pot microwave-mediated synthesis

KW - Water

UR - http://hdl.handle.net/10807/195388

U2 - 10.1039/c9ob01962f

DO - 10.1039/c9ob01962f

M3 - Article

SN - 1477-0520

VL - 17

SP - 8982

EP - 8986

JO - ORGANIC & BIOMOLECULAR CHEMISTRY

JF - ORGANIC & BIOMOLECULAR CHEMISTRY

ER -

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

Abstract

Keywords

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