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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407413
Subject(s) - singlet oxygen , chemistry , nucleophile , photochemistry , alcohol , singlet state , oxygen , nucleophilic addition , primary (astronomy) , medicinal chemistry , catalysis , organic chemistry , physics , astronomy , nuclear physics , excited state
Abstract 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.