✍ Scribed by Chu-Yi Yu; David L. Taylor; Otto Meth-Cohn
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Pseudo Vilsmeier Reagents. A New Protocol for Regiospecific C-C Bond Formation in Pyridines.
-A new approach to functionalize π-deficient heterocycles particularly with carbon-based groups involves the reaction of in situ generated pseudo-Vilsmeier pyridinium salts (III) and (VIII) with electrophilic enamines to give new α-functionalized pyridinium salts (V), (X), and (XII). These products can be either reduced to give the corresponding keto-1,2,3,6-tetrahydropyridines, or hydrolyzed to give the corresponding ketopyridines, or hydrogenated to give ketopiperidines.
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