Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes

Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphili...

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Autores principales: Li, De-Yao, Wei, Yin, Marek, Ilan, Tang, Xiang-Ying, Shi, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5949847/
https://www.ncbi.nlm.nih.gov/pubmed/29861890
http://dx.doi.org/10.1039/c5sc01806d
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author Li, De-Yao
Wei, Yin
Marek, Ilan
Tang, Xiang-Ying
Shi, Min
author_facet Li, De-Yao
Wei, Yin
Marek, Ilan
Tang, Xiang-Ying
Shi, Min
author_sort Li, De-Yao
collection PubMed
description Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphilic strategy to generate a gold carbene via a rearrangement of vinylidenecyclopropane. Whereas, the electronic effect of the ortho-substituents switches the reaction mode onto the non-carbene related process, from which five- or six-membered rings are selectively produced through allyl-migration.
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spelling pubmed-59498472018-06-01 Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes Li, De-Yao Wei, Yin Marek, Ilan Tang, Xiang-Ying Shi, Min Chem Sci Chemistry Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphilic strategy to generate a gold carbene via a rearrangement of vinylidenecyclopropane. Whereas, the electronic effect of the ortho-substituents switches the reaction mode onto the non-carbene related process, from which five- or six-membered rings are selectively produced through allyl-migration. Royal Society of Chemistry 2015-10-01 2015-06-24 /pmc/articles/PMC5949847/ /pubmed/29861890 http://dx.doi.org/10.1039/c5sc01806d Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Li, De-Yao
Wei, Yin
Marek, Ilan
Tang, Xiang-Ying
Shi, Min
Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
title Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
title_full Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
title_fullStr Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
title_full_unstemmed Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
title_short Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
title_sort gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5949847/
https://www.ncbi.nlm.nih.gov/pubmed/29861890
http://dx.doi.org/10.1039/c5sc01806d
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