Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins

[Image: see text] The application of organocatalytic bifunctional activation in the remote (3 + 2)-cycloaddition between 4-(alk-1-en-1-yl)-3-cyanocoumarins and imines derived from salicylaldehyde is demonstrated. Products, bearing two biologically relevant units, have been obtained with good chemica...

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Autores principales: Łukasik, Beata, Romaniszyn, Marta, Kłoszewski, Nathan, Albrecht, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10226170/
https://www.ncbi.nlm.nih.gov/pubmed/37186962
http://dx.doi.org/10.1021/acs.orglett.3c01189
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author Łukasik, Beata
Romaniszyn, Marta
Kłoszewski, Nathan
Albrecht, Łukasz
author_facet Łukasik, Beata
Romaniszyn, Marta
Kłoszewski, Nathan
Albrecht, Łukasz
author_sort Łukasik, Beata
collection PubMed
description [Image: see text] The application of organocatalytic bifunctional activation in the remote (3 + 2)-cycloaddition between 4-(alk-1-en-1-yl)-3-cyanocoumarins and imines derived from salicylaldehyde is demonstrated. Products, bearing two biologically relevant units, have been obtained with good chemical and stereochemical efficiency. The stereochemical outcome of the process results from the application of a quinine-derived catalyst. Selected transformations of the cycloadducts leading to further chemical diversity have been demonstrated.
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spelling pubmed-102261702023-05-30 Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins Łukasik, Beata Romaniszyn, Marta Kłoszewski, Nathan Albrecht, Łukasz Org Lett [Image: see text] The application of organocatalytic bifunctional activation in the remote (3 + 2)-cycloaddition between 4-(alk-1-en-1-yl)-3-cyanocoumarins and imines derived from salicylaldehyde is demonstrated. Products, bearing two biologically relevant units, have been obtained with good chemical and stereochemical efficiency. The stereochemical outcome of the process results from the application of a quinine-derived catalyst. Selected transformations of the cycloadducts leading to further chemical diversity have been demonstrated. American Chemical Society 2023-05-15 /pmc/articles/PMC10226170/ /pubmed/37186962 http://dx.doi.org/10.1021/acs.orglett.3c01189 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Łukasik, Beata
Romaniszyn, Marta
Kłoszewski, Nathan
Albrecht, Łukasz
Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
title Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
title_full Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
title_fullStr Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
title_full_unstemmed Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
title_short Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
title_sort asymmetric organocatalysis in the remote (3 + 2)-cycloaddition to 4-(alk-1-en-1-yl)-3-cyanocoumarins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10226170/
https://www.ncbi.nlm.nih.gov/pubmed/37186962
http://dx.doi.org/10.1021/acs.orglett.3c01189
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AT kłoszewskinathan asymmetricorganocatalysisintheremote32cycloadditionto4alk1en1yl3cyanocoumarins
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