Abstract
AbstractExploration of the repurposing of N-acyl chiral auxiliaries for use as novel chiral C1 radical synthons is reported. The acyl radicals are generated under visible-light-mediated single-electron transfer of N-hydroxyphthalimido ester, and their use toward the stereoselective synthesis of 3,3-disubstituted oxindoles via a radical addition–cyclisation sequence is demonstrated. The downstream synthetic utility of this method is showcased in the formal synthesis of the natural product (–)-physovenine. TEMPO trapping experiments support the proposed reaction mechanism.
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