Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction

[Image: see text] In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the...

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Autores principales: Saktura, Maciej, Grzelak, Paulina, Dybowska, Joanna, Albrecht, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497662/
https://www.ncbi.nlm.nih.gov/pubmed/32065757
http://dx.doi.org/10.1021/acs.orglett.0c00138
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author Saktura, Maciej
Grzelak, Paulina
Dybowska, Joanna
Albrecht, Łukasz
author_facet Saktura, Maciej
Grzelak, Paulina
Dybowska, Joanna
Albrecht, Łukasz
author_sort Saktura, Maciej
collection PubMed
description [Image: see text] In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the formation of biologically relevant [2.2.2]-bicyclic lactones. Their functionalization potential has been confirmed in selected, diastereoselective transformations.
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spelling pubmed-74976622020-09-18 Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction Saktura, Maciej Grzelak, Paulina Dybowska, Joanna Albrecht, Łukasz Org Lett [Image: see text] In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the formation of biologically relevant [2.2.2]-bicyclic lactones. Their functionalization potential has been confirmed in selected, diastereoselective transformations. American Chemical Society 2020-02-17 2020-03-06 /pmc/articles/PMC7497662/ /pubmed/32065757 http://dx.doi.org/10.1021/acs.orglett.0c00138 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Saktura, Maciej
Grzelak, Paulina
Dybowska, Joanna
Albrecht, Łukasz
Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
title Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
title_full Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
title_fullStr Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
title_full_unstemmed Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
title_short Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
title_sort asymmetric synthesis of [2.2.2]-bicyclic lactones via all-carbon inverse-electron-demand diels–alder reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497662/
https://www.ncbi.nlm.nih.gov/pubmed/32065757
http://dx.doi.org/10.1021/acs.orglett.0c00138
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