Chiral Acyl Radicals Generated by Visible Light Enable Stereoselective Access to 3,3-Disubstituted Oxindoles: Application toward the Synthesis of (–)- and (+)-Physovenine

Josef Späth; Meghan J. Oddy; Roger Hunter; Wade F. Petersen

doi:10.1055/a-1959-1930

Synthesis, Table of Contents

Synthesis 2023; 55(11): 1736-1743
DOI: 10.1055/a-1959-1930

paper

Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Chiral Acyl Radicals Generated by Visible Light Enable Stereoselective Access to 3,3-Disubstituted Oxindoles: Application toward the Synthesis of (–)- and (+)-Physovenine

Josef Späth

,

Meghan J. Oddy

,

Roger Hunter

,

Wade F. Petersen ∗

Abstract

All articles of this category

Abstract

Exploration 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.

Key words

photocatalysis - acyl radicals - C–H functionalisation - oxindoles - natural products - stereoselective synthesis

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