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 hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product

Enantioselective C–C Bond Formation during the Oxidation of 5‑Phenylpent-2-enyl Carboxylates with Hypervalent Iodine(III)

The oxidation of (5-acyloxypent-3-enyl)­benzene with hypervalent iodine­(III) afforded 2-oxy-1-(oxymethyl)­tetrahydronaphthalene under metal-free conditions. The acyloxy group may nucleophilically participate in the oxidative cyclization. A lactate-based chiral hypervalent iodine afforded an enantioselective variant of oxyarylation with up to 89% ee

Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide Metabolites Using Chiral Hypervalent Iodine(III)

Stereoselective oxylactonization of <i>ortho</i>-alkenylbenzoate with chiral hypervalent iodine is applied to the asymmetric synthesis of 4-oxyisochroman-1-one polyketide metabolites including 4-hydroxymellein (<b>1</b>), a derivative of fusarentin <b>2</b>, monocerin (<b>3</b>), and an epimer of monocerin <i>epi</i>-<b>3</b>

Synthesis of Chiral Tritylpyrrolidine Derivatives and Their Application to Asymmetric Benzoyloxylation

An efficient synthesis of novel chiral tritylpyrrolidine derivatives has been developed. Single stereoisomers of various tritylpyrrolidine derivatives can be readily obtained through diastereomer separation by simple silica gel column chromatography. Representative compounds of this class have been shown to be efficient amine organocatalysts for asymmetric benzoyloxylation