Issue 21, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 aug 2018
Accepted
26 sep 2018
First published
26 sep 2018

Org. Chem. Front., 2018,5, 3129-3132

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, 5, 3129 DOI: 10.1039/C8QO00803E

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