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Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner-Wadsworth-Emmons (HWE) Olefination.

Xing-Gui ZhangXin LiChi ZhangChao Feng
Published in: Organic letters (2021)
An efficient telescoped method for the rapid assembly of multisubstituted cyclohexenes is presented herein. The whole process nicely merges photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner-Wadsworth-Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.
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