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

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...

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Veröffentlicht in:Synthesis (Stuttgart) 2023-06, Vol.55 (11), p.1736-1743
Hauptverfasser: Späth, Josef, Oddy, Meghan J., Hunter, Roger, Petersen, Wade F.
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1959-1930