5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene

[Image: see text] This study demonstrates the use of organocatalytic Brønsted base activation of 5-substituted-furan-2(3H)-ones to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition involving 8,8-dicyanoheptafulvene as an 8π-component. The use of dienolates in a higher-order cyc...

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Autores principales: Romaniszyn, Marta, Sieroń, Lesław, Albrecht, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016758/
https://www.ncbi.nlm.nih.gov/pubmed/35349288
http://dx.doi.org/10.1021/acs.joc.2c00101
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author Romaniszyn, Marta
Sieroń, Lesław
Albrecht, Łukasz
author_facet Romaniszyn, Marta
Sieroń, Lesław
Albrecht, Łukasz
author_sort Romaniszyn, Marta
collection PubMed
description [Image: see text] This study demonstrates the use of organocatalytic Brønsted base activation of 5-substituted-furan-2(3H)-ones to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition involving 8,8-dicyanoheptafulvene as an 8π-component. The use of dienolates in a higher-order cycloaddition reaction leads to the formation of biologically relevant polycyclic products bearing a γ-butyrolactone structural motif, thus broadening the synthetic potential of Brønsted base activated higher-order cycloadditions.
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spelling pubmed-90167582022-04-20 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene Romaniszyn, Marta Sieroń, Lesław Albrecht, Łukasz J Org Chem [Image: see text] This study demonstrates the use of organocatalytic Brønsted base activation of 5-substituted-furan-2(3H)-ones to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition involving 8,8-dicyanoheptafulvene as an 8π-component. The use of dienolates in a higher-order cycloaddition reaction leads to the formation of biologically relevant polycyclic products bearing a γ-butyrolactone structural motif, thus broadening the synthetic potential of Brønsted base activated higher-order cycloadditions. American Chemical Society 2022-03-29 2022-04-15 /pmc/articles/PMC9016758/ /pubmed/35349288 http://dx.doi.org/10.1021/acs.joc.2c00101 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
Sieroń, Lesław
Albrecht, Łukasz
5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
title 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
title_full 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
title_fullStr 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
title_full_unstemmed 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
title_short 5-Substituted-furan-2(3H)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
title_sort 5-substituted-furan-2(3h)-ones in [8 + 2]-cycloaddition with 8,8-dicyanoheptafulvene
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016758/
https://www.ncbi.nlm.nih.gov/pubmed/35349288
http://dx.doi.org/10.1021/acs.joc.2c00101
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