Metal-promoted variants of the Passerini reaction leading to functionalized heterocycles.
[reaction: see text]. The effect of replacing the Brønsted acid in classic Passerini reactions with a mild Lewis acid has been studied. Triggered by metal-promoted silylation, condensations of aliphatic or aromatic carbonyl compounds with appropriately substituted isonitriles capable of neighboring group donation afford alpha-hydroxyamides, substituted oxazoles, and other useful heterocycles.
Xia
Qian
Q
Department of Chemistry & Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Ganem
Bruce
B
D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007700:Kinetics; D008670:Metals / Q000737:chemistry
D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D008670:Metals