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Volume 20
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10.3390/molecules200917041
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Article

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

by
Mio Shimogaki
,
Morifumi Fujita
* and
Takashi Sugimura
Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan
*
Author to whom correspondence should be addressed.
Molecules 2015, 20(9), 17041-17057; https://doi.org/10.3390/molecules200917041
Submission 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.
Keywords: hypervalent iodine; oxidation; dioxolane; dioxolanyl cation; stereoselective synthesis hypervalent iodine; oxidation; dioxolane; dioxolanyl cation; stereoselective synthesis
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MDPI and ACS Style

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. https://doi.org/10.3390/molecules200917041

AMA Style

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(9):17041-17057. https://doi.org/10.3390/molecules200917041

Chicago/Turabian Style

Shimogaki, Mio, Morifumi Fujita, and Takashi Sugimura. 2015. "Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)" Molecules 20, no. 9: 17041-17057. https://doi.org/10.3390/molecules200917041

APA Style

Shimogaki, M., Fujita, M., & Sugimura, T. (2015). Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III). Molecules, 20(9), 17041-17057. https://doi.org/10.3390/molecules200917041

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