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Molecules 2015, 20(9), 17041-17057; doi:10.3390/molecules200917041

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

Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan
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Author to whom correspondence should be addressed.
Academic Editors: Wesley Moran and Arantxa Rodríguez
Received: 14 August 2015 / Revised: 9 September 2015 / Accepted: 11 September 2015 / Published: 17 September 2015
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Abstract

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. View Full-Text
Keywords: hypervalent iodine; oxidation; dioxolane; dioxolanyl cation; stereoselective synthesis hypervalent iodine; oxidation; dioxolane; dioxolanyl cation; stereoselective synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Shimogaki, M.; Fujita, M.; Sugimura, T. Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III). Molecules 2015, 20, 17041-17057.

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