Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis

[Image: see text] A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of thia-Michael/aldol/annulation reactions. This highly diastereo- and e...

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Autores principales: Romaniszyn, Marta, Skrzyńska, Anna, Dybowska, Joanna, Albrecht, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9623593/
https://www.ncbi.nlm.nih.gov/pubmed/36252955
http://dx.doi.org/10.1021/acs.orglett.2c02836
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author Romaniszyn, Marta
Skrzyńska, Anna
Dybowska, Joanna
Albrecht, Łukasz
author_facet Romaniszyn, Marta
Skrzyńska, Anna
Dybowska, Joanna
Albrecht, Łukasz
author_sort Romaniszyn, Marta
collection PubMed
description [Image: see text] A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of thia-Michael/aldol/annulation reactions. This highly diastereo- and enantioselective reaction is realized by employing enantioselective bifunctional catalysis and exhibits a broad substrate scope and excellent functional group tolerance. The synthetic application involves the transformation of the imidoester group, thus opening access to biologically relevant coumarin and δ-lactone-fused products.
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spelling pubmed-96235932022-11-02 Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis Romaniszyn, Marta Skrzyńska, Anna Dybowska, Joanna Albrecht, Łukasz Org Lett [Image: see text] A novel organocatalytic reaction cascade between 3-cyano-4-styrylcoumarins and 2-mercaptoacetophenones is described. It is based on stereocontrolled functionalization of cyanocoumarins proceeding in a sequence of thia-Michael/aldol/annulation reactions. This highly diastereo- and enantioselective reaction is realized by employing enantioselective bifunctional catalysis and exhibits a broad substrate scope and excellent functional group tolerance. The synthetic application involves the transformation of the imidoester group, thus opening access to biologically relevant coumarin and δ-lactone-fused products. American Chemical Society 2022-10-17 2022-10-28 /pmc/articles/PMC9623593/ /pubmed/36252955 http://dx.doi.org/10.1021/acs.orglett.2c02836 Text en © 2022 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 Romaniszyn, Marta
Skrzyńska, Anna
Dybowska, Joanna
Albrecht, Łukasz
Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
title Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
title_full Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
title_fullStr Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
title_full_unstemmed Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
title_short Organocatalytic Asymmetric Approach to γ,δ-Functionalization of 3-Cyano-4-styrylcoumarins via Bifunctional Catalysis
title_sort organocatalytic asymmetric approach to γ,δ-functionalization of 3-cyano-4-styrylcoumarins via bifunctional catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9623593/
https://www.ncbi.nlm.nih.gov/pubmed/36252955
http://dx.doi.org/10.1021/acs.orglett.2c02836
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