Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

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

Enantioselective C–C Bond Formation during the Oxidation of 5-Phenylpent-2-enyl Carboxylates with Hypervalent Iodine(III)
Mio Shimogaki, Takashi Sugimura, Morifumi Fujita
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01141

DOI: 10.1021/acs.joc.7b01141

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