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

Title Enantioselective C-C Bond Formation during the Oxidation of 5-Phenylpent-2-enyl Carboxylates with Hypervalent Iodine(III).
Authors M. Shimogaki; M. Fujita; T. Sugimura
Journal J Org Chem
DOI 10.1021/acs.joc.7b01141
Abstract

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.

Citation M. Shimogaki; M. Fujita; T. Sugimura.Enantioselective C-C Bond Formation during the Oxidation of 5-Phenylpent-2-enyl Carboxylates with Hypervalent Iodine(III).. J Org Chem. 2017. doi:10.1021/acs.joc.7b01141

Related Elements

Iodine

See more Iodine products. Iodine (atomic symbol: I, atomic number: 53) is a Block P, Group 17, Period 5 element with an atomic radius of 126.90447. The number of electrons in each of Iodine's shells is 2, 8, 18, 18, 7 and its electron configuration is [Kr] 4d10 5s2 5p5. The iodine atom has a radius of 140 pm and a Van der Waals radius of 198 pm. In its elemental form, iodine has a lustrous metallic gray appearance as a solid and a violet appearance as a gas or liquid solution. Elemental IodineIodine forms compounds with many elements, but is less active than the other halogens. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide. Iodine compounds are important in organic chemistry and very useful in the field of medicine. Iodine was discovered and first isolated by Bernard Courtois in 1811. The name Iodine is derived from the Greek word "iodes" meaning violet.

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