학술논문
Chiral Acyl Radicals Generated by Visible Light Enable Stereoselective Access to 3,3-Disubstituted Oxindoles: Application toward the Synthesis of (–)- and (+)-Physovenine.
Document Type
Article
Source
Subject
*OXINDOLES
*RADICALS (Chemistry)
*VISIBLE spectra
*STEREOSELECTIVE reactions
*NATURAL products
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Language
ISSN
0039-7881
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. [ABSTRACT FROM AUTHOR]