Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 24, Pages 5591-5601Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00308e
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- Centre National de la Recherche Scientifique
- Museum National d'Histoire Naturelle
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This contribution describes the synthesis of several novel bicyclic alpha-amino endoperoxides, including CF3-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich-de Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented.
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