title: Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III).
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.
authors.affiliation: Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan. rk14v001@stkt.u-hyogo.ac.jp.
authors.forename: Mio
authors.initials: M
authors.lastname: Shimogaki
authors.affiliation: Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan. fuji@sci.u-hyogo.ac.jp.
authors.forename: Morifumi
authors.initials: M
authors.lastname: Fujita
authors.affiliation: Graduate School of Material Science, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan. sugimura@sci.u-hyogo.ac.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Sugimura
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D004148:Dioxolanes / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004148:Dioxolanes; D007455:Iodine
keywords: dioxolane; dioxolanyl cation; hypervalent iodine; oxidation; stereoselective synthesis