Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold

(1R*,4S*,4aR*,9aS*,10S*)-10-Hydroxy-10-phenyl-1,4a,9a,10-tetrahydro-1,4-methanoanthracen-9(4H)-one (1c) was prepared for the elucidation of the reaction mechanism of intramolecular hydroalkoxylation of alkenes catalyzed by gold nanoclusters stabilized by a hydrophilic polymer, poly(N-vinyl-2-pyrroli...

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Detalles Bibliográficos
Autores principales: Kitahara, Hiroaki, Sakurai, Hidehiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268499/
https://www.ncbi.nlm.nih.gov/pubmed/22388968
http://dx.doi.org/10.3390/molecules17032579
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author Kitahara, Hiroaki
Sakurai, Hidehiro
author_facet Kitahara, Hiroaki
Sakurai, Hidehiro
author_sort Kitahara, Hiroaki
collection PubMed
description (1R*,4S*,4aR*,9aS*,10S*)-10-Hydroxy-10-phenyl-1,4a,9a,10-tetrahydro-1,4-methanoanthracen-9(4H)-one (1c) was prepared for the elucidation of the reaction mechanism of intramolecular hydroalkoxylation of alkenes catalyzed by gold nanoclusters stabilized by a hydrophilic polymer, poly(N-vinyl-2-pyrrolidone) (Au:PVP). It was found that the reaction proceeded via anti-addition of alcohol to the alkene assisted by π-activation of the gold clusters, which is the same mechanism as the hydroamination by toluenesulfonamides.
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spelling pubmed-62684992018-12-20 Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold Kitahara, Hiroaki Sakurai, Hidehiro Molecules Communication (1R*,4S*,4aR*,9aS*,10S*)-10-Hydroxy-10-phenyl-1,4a,9a,10-tetrahydro-1,4-methanoanthracen-9(4H)-one (1c) was prepared for the elucidation of the reaction mechanism of intramolecular hydroalkoxylation of alkenes catalyzed by gold nanoclusters stabilized by a hydrophilic polymer, poly(N-vinyl-2-pyrrolidone) (Au:PVP). It was found that the reaction proceeded via anti-addition of alcohol to the alkene assisted by π-activation of the gold clusters, which is the same mechanism as the hydroamination by toluenesulfonamides. MDPI 2012-03-02 /pmc/articles/PMC6268499/ /pubmed/22388968 http://dx.doi.org/10.3390/molecules17032579 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Communication
Kitahara, Hiroaki
Sakurai, Hidehiro
Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold
title Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold
title_full Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold
title_fullStr Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold
title_full_unstemmed Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold
title_short Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold
title_sort anti-addition mechanism in the intramolecular hydroalkoxylation of alkenes catalyzed by pvp-stabilized nanogold
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268499/
https://www.ncbi.nlm.nih.gov/pubmed/22388968
http://dx.doi.org/10.3390/molecules17032579
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