The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones

Imidazolidine-4-thiones have been suggested as potential prebiotic organocatalysts for light-driven α-alkylations of aldehydes by bromoacetonitrile. However, imidazolidine-4-thiones react with bromoacetonitrile to give S-cyanomethylated dihydroimidazoles. Kinetic studies show that enamines derived f...

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Detalles Bibliográficos
Autores principales: Hensinger, Magenta J., Closs, Anna C., Trapp, Oliver, Ofial, Armin R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10297834/
https://www.ncbi.nlm.nih.gov/pubmed/37293771
http://dx.doi.org/10.1039/d3cc01912h
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author Hensinger, Magenta J.
Closs, Anna C.
Trapp, Oliver
Ofial, Armin R.
author_facet Hensinger, Magenta J.
Closs, Anna C.
Trapp, Oliver
Ofial, Armin R.
author_sort Hensinger, Magenta J.
collection PubMed
description Imidazolidine-4-thiones have been suggested as potential prebiotic organocatalysts for light-driven α-alkylations of aldehydes by bromoacetonitrile. However, imidazolidine-4-thiones react with bromoacetonitrile to give S-cyanomethylated dihydroimidazoles. Kinetic studies show that enamines derived from these cyclic secondary amines and aldehydes are more nucleophilic than enamines derived from aldehydes and MacMillan organocatalysts.
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spelling pubmed-102978342023-06-28 The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones Hensinger, Magenta J. Closs, Anna C. Trapp, Oliver Ofial, Armin R. Chem Commun (Camb) Chemistry Imidazolidine-4-thiones have been suggested as potential prebiotic organocatalysts for light-driven α-alkylations of aldehydes by bromoacetonitrile. However, imidazolidine-4-thiones react with bromoacetonitrile to give S-cyanomethylated dihydroimidazoles. Kinetic studies show that enamines derived from these cyclic secondary amines and aldehydes are more nucleophilic than enamines derived from aldehydes and MacMillan organocatalysts. The Royal Society of Chemistry 2023-06-09 /pmc/articles/PMC10297834/ /pubmed/37293771 http://dx.doi.org/10.1039/d3cc01912h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Hensinger, Magenta J.
Closs, Anna C.
Trapp, Oliver
Ofial, Armin R.
The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
title The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
title_full The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
title_fullStr The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
title_full_unstemmed The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
title_short The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
title_sort effect of s-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10297834/
https://www.ncbi.nlm.nih.gov/pubmed/37293771
http://dx.doi.org/10.1039/d3cc01912h
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