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

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journal contribution
posted on 29.05.2017, 00:00 by Mio Shimogaki, Morifumi Fujita, Takashi Sugimura
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.