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      Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

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          Summary

          The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers.

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          Most cited references 53

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          Modern strategies in electroorganic synthesis.

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            The application of cathodic reductions and anodic oxidations in the synthesis of complex molecules.

             D. Wright,  B Sperry (2006)
            This tutorial review surveys the recent advances in electrochemical transformations as they pertain to the synthesis of complex organic molecules. Electrochemistry has emerged as a powerful tool to synthetic chemists, yet many have never considered electrochemical methodology as a means for synthesis. Here, an introduction to electrochemistry and voltammetry will be provided with descriptions of the four types of electrochemical cells. In addition, recent examples of both anodic oxidations and cathodic reductions will be discussed, along with the experimental setups for carrying out each reaction.
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              Synthetic Applications of Anodic Electrochemistry

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                Author and article information

                Contributors
                Role: Guest Editor
                Journal
                Beilstein J Org Chem
                Beilstein J Org Chem
                Beilstein Journal of Organic Chemistry
                Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                1860-5397
                2015
                28 January 2015
                : 11
                : 174-183
                Affiliations
                [1 ]Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35043 Marburg, Germany
                [2 ]Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
                Article
                10.3762/bjoc.11.18
                4361995
                25815067
                Copyright © 2015, Röse et al; licensee Beilstein-Institut.

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                Categories
                Full Research Paper
                Chemistry
                Organic Chemistry

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