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Electrochemical synthesis of 7-membered carbocycles through cascade 5-exo-trig/7-endo-trig radical cyclization

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Abstract

7-endo-trig cyclizations, especially for unhindered terminal alkenes, remain underdeveloped. We report herein an electrochemical synthesis of functionalized 7-membered carbocycles through a 5-exo-trig/7-endo-trig radical cyclization cascade. The first cyclization step of the cascade process forms a 5-membered ring with trans-disposition of the radical center and the remaining alkene. This trans configuration forces the 6-heptenyl radical to undergo regioselective 7-endo cyclization.

Graphical abstract: Electrochemical synthesis of 7-membered carbocycles through cascade 5-exo-trig/7-endo-trig radical cyclization

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Publication details

The article was received on 01 Aug 2018, accepted on 26 Sep 2018 and first published on 26 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00803E
Citation: Org. Chem. Front., 2018, Advance Article
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    Electrochemical synthesis of 7-membered carbocycles through cascade 5-exo-trig/7-endo-trig radical cyclization

    H. Long, J. Song and H. Xu, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00803E

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