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Visible‐Light‐Mediated 1,2‐Acyl Migration: The Reaction of Secondary Enamino Ketones with Singlet Oxygen
Author(s) -
Fan Weigang,
Li Pixu
Publication year - 2014
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.201407413
Subject(s) - singlet oxygen , chemistry , nucleophile , photochemistry , singlet state , alcohol , oxygen , medicinal chemistry , catalysis , organic chemistry , physics , nuclear physics , excited state
Secondary enaminones were oxidized by photochemically generated singlet oxygen, followed by nucleophilic addition of alcohol and an unexpected 1,2‐acyl migration to afford quaternary amino acid derivatives. An ene‐type reaction pathway is proposed. It is distinctively different from the typical [2+2] addition of singlet oxygen to a CC bond pathway.