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Chemoselective γ‐Oxidation of β,γ‐Unsaturated Amides with TEMPO
Author(s) -
Heindl Sebastian,
Riomet Margaux,
Matyasovsky Ján,
Lemmerer Miran,
Malzer Nicolas,
Maulide Nuno
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202104023
Subject(s) - regioselectivity , amide , electrophile , chemistry , organic chemistry , chemoselectivity , combinatorial chemistry , catalysis
A chemoselective and robust protocol for the γ‐oxidation of β,γ‐unsaturated amides is reported. In this method, electrophilic amide activation, in a rare application to unsaturated amides, enables a regioselective reaction with TEMPO resulting in the title products. Radical cyclisation reactions and oxidation of the synthesised products highlight the synthetic utility of the products obtained.