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

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 racemate...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-10, Vol.17 (4), p.8982-8986
Main Authors: Lauder, Kate, Masci, Domiziana, Toscani, Anita, Al Mekdad, Aya, Black, Gary W, Brown, Nicola L, Turner, Nicholas J, Luisi, Renzo, Castagnolo, Daniele
Format: Article
Language:English
Subjects:
Amine oxidase (flavin-containing)
Amines - chemical synthesis
Amines - chemistry
Amines - metabolism
Aromatic compounds
Biocatalysis
Biocatalysts
Intermediates
Microwaves
Models, Molecular
Molecular Structure
Monoamine Oxidase - chemistry
Monoamine Oxidase - metabolism
Oxidase
Stereoisomerism
Synthesis
Water - chemistry
Water - metabolism
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Summary: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. A microwave assisted multicomponent protocol on water allows the regioselective synthesis of chiral aryl-1,2-mercaptoamines. The enzymatic resolution of the racemates leads to enantioenriched products.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01962f