Literature DB >> 23552389

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

Yosuke Ashikari1, Toshiki Nokami, Jun-ichi Yoshida.   

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.

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Year:  2013        PMID: 23552389     DOI: 10.1039/c3ob40315g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  7 in total

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Authors:  Ming Yan; Yu Kawamata; Phil S Baran
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2.  Oxidative cyclization reactions: controlling the course of a radical cation-derived reaction with the use of a second nucleophile.

Authors:  Alison Redden; Robert J Perkins; Kevin D Moeller
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-19       Impact factor: 15.336

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Authors:  Tomasz Wdowik; Sherry R Chemler
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4.  Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - synthesis of halohydrins and epoxides.

Authors:  Akihiro Shimizu; Ryutaro Hayashi; Yosuke Ashikari; Toshiki Nokami; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2015-02-13       Impact factor: 2.883

Review 5.  Recent advances in the electrochemical construction of heterocycles.

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Authors:  Toshiki Nokami; Naoki Musya; Tatsuya Morofuji; Keiji Takeda; Masahiro Takumi; Akihiro Shimizu; Jun-Ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2014-12-22       Impact factor: 2.883

7.  Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor.

Authors:  Yuki Naito; Naoki Shida; Mahito Atobe
Journal:  Beilstein J Org Chem       Date:  2022-03-29       Impact factor: 2.883

  7 in total

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