N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate

The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this s...

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Detalles Bibliográficos
Autores principales: Chen, Xiang-Yu, Chen, Kun-Quan, Sun, De-Qun, Ye, Song
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5384455/
https://www.ncbi.nlm.nih.gov/pubmed/28451308
http://dx.doi.org/10.1039/c6sc04135c
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author Chen, Xiang-Yu
Chen, Kun-Quan
Sun, De-Qun
Ye, Song
author_facet Chen, Xiang-Yu
Chen, Kun-Quan
Sun, De-Qun
Ye, Song
author_sort Chen, Xiang-Yu
collection PubMed
description The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this strategy. The oxidative cross coupling of homoenolate and enolate via single electron transfer was proposed as the key step for the reaction.
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spelling pubmed-53844552017-04-27 N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate Chen, Xiang-Yu Chen, Kun-Quan Sun, De-Qun Ye, Song Chem Sci Chemistry The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this strategy. The oxidative cross coupling of homoenolate and enolate via single electron transfer was proposed as the key step for the reaction. Royal Society of Chemistry 2017-03-01 2016-11-09 /pmc/articles/PMC5384455/ /pubmed/28451308 http://dx.doi.org/10.1039/c6sc04135c Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Chen, Xiang-Yu
Chen, Kun-Quan
Sun, De-Qun
Ye, Song
N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
title N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
title_full N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
title_fullStr N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
title_full_unstemmed N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
title_short N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
title_sort n-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5384455/
https://www.ncbi.nlm.nih.gov/pubmed/28451308
http://dx.doi.org/10.1039/c6sc04135c
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