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Synthesis 2023; 55(11): 1736-1743
DOI: 10.1055/a-1959-1930
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
The authors would like to thank the Royal Society and the African Academy of Sciences (FLR\R1\190531), the Royal Society of Chemistry (RF21-7183233767), the National Research Foundation (W.F.P., grant no.: 138082), and the University of Cape Town (W.F.P.; M.J.O.; J.S. [UCT, B.R.A.A.S]) for their funding contributions.
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1959-1930.
- Supporting Information
Publication History
Received: 09 September 2022
Accepted: 12 October 2022
Accepted Manuscript online:
12 October 2022
Article published online:
08 December 2022
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For selected reviews on radical cascades, see:
Recent reviews on photoinduced acyl radical chemistry:
See also: