Metal-Promoted Variants of the Passerini Reaction Leading to Functionalized Heterocycles

Abstract

[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.