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^*

^*Corresponding author for this work

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

6 Citations (Scopus)

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	E-pub ahead of print - 25 Sept 2019

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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 AND BIOMOLECULAR CHEMISTRY, 17(40), 8982-8986. Advance online publication. https://doi.org/10.1039/c9ob01962f

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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.",

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",

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doi = "10.1039/c9ob01962f",

language = "English",

volume = "17",

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journal = "ORGANIC AND BIOMOLECULAR CHEMISTRY",

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Lauder, K, Masci, D, Toscani, A, Al Mekdad, A, Black, GW, Brown, NL, 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

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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 - 2019/9/25

Y1 - 2019/9/25

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.

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U2 - 10.1039/c9ob01962f

DO - 10.1039/c9ob01962f

M3 - Article

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AN - SCOPUS:85073488621

SN - 1477-0520

VL - 17

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JO - ORGANIC AND BIOMOLECULAR CHEMISTRY

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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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