Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)

Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hyper...

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Detalles Bibliográficos
Autores principales: Shimogaki, Mio, Fujita, Morifumi, Sugimura, Takashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332268/
https://www.ncbi.nlm.nih.gov/pubmed/26393548
http://dx.doi.org/10.3390/molecules200917041
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author Shimogaki, Mio
Fujita, Morifumi
Sugimura, Takashi
author_facet Shimogaki, Mio
Fujita, Morifumi
Sugimura, Takashi
author_sort Shimogaki, Mio
collection PubMed
description Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product.
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spelling pubmed-63322682019-01-24 Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III) Shimogaki, Mio Fujita, Morifumi Sugimura, Takashi Molecules Article Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product. MDPI 2015-09-17 /pmc/articles/PMC6332268/ /pubmed/26393548 http://dx.doi.org/10.3390/molecules200917041 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shimogaki, Mio
Fujita, Morifumi
Sugimura, Takashi
Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
title Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
title_full Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
title_fullStr Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
title_full_unstemmed Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
title_short Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
title_sort stereoselective formation of substituted 1,3-dioxolanes through a three-component assembly during the oxidation of alkenes with hypervalent iodine(iii)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332268/
https://www.ncbi.nlm.nih.gov/pubmed/26393548
http://dx.doi.org/10.3390/molecules200917041
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AT fujitamorifumi stereoselectiveformationofsubstituted13dioxolanesthroughathreecomponentassemblyduringtheoxidationofalkeneswithhypervalentiodineiii
AT sugimuratakashi stereoselectiveformationofsubstituted13dioxolanesthroughathreecomponentassemblyduringtheoxidationofalkeneswithhypervalentiodineiii

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