Issue 20, 2013
From the journal:

Organic & Biomolecular Chemistry

Integration of electrooxidative cyclization and chemical oxidationvia alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization†

Yosuke Ashikari,a   Toshiki Nokamia  and  Jun-ichi Yoshida*a  

* Corresponding authors

a Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, 615-8510 Kyoto, Japan
E-mail: yoshida@sbchem.kyoto-u.ac.jp
Fax: +81-75-383-2725
Tel: +81-75-383-2726

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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Article information

DOI
https://doi.org/10.1039/C3OB40315G
Article type
Paper
Submitted
13 Feb 2013
Accepted
18 Mar 2013
First published
19 Mar 2013

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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