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Issue 20, 2013
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Integration of electrooxidative cyclization and chemical oxidationvia alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization

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Abstract

An integration of electrooxidative cyclization and chemical oxidation was achieved. Electrochemical oxidation of alkenes having a nucleophilic moiety in the presence of DMSO gave cyclized alkoxysulfonium ions, which were converted to the corresponding ketones by treatment with triethylamine in a one-pot sequential manner. The method is also an effective tool for cyclization of 1,6-dienes affording five-membered ring diketones in high stereoselectivity.

Graphical abstract: Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization

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Publication details

The article was received on 13 Feb 2013, accepted on 18 Mar 2013 and first published on 19 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40315G
Org. Biomol. Chem., 2013,11, 3322-3331

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    Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization

    Y. Ashikari, T. Nokami and J. Yoshida, Org. Biomol. Chem., 2013, 11, 3322
    DOI: 10.1039/C3OB40315G

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