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

Org Lett. 2021 Dec 17;23(24):9611-9615. doi: 10.1021/acs.orglett.1c03821. Epub 2021 Dec 6.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't