Copper-catalyzed Perkin-acyl-Mannich reaction of acetic anhydride with pyridine: expeditious entry to unconventional piperidines.

A regioselective introduction of a methoxycarbonyl methyl group at the C(2) position of unsubstituted pyridine has been accomplished with catalytic amounts of copper(II) triflate in mild reaction conditions. The N-acetyl-1,2-dihydropyridyl acetic acid methyl ester obtained is a valuable building block for the synthesis of new polyfunctionalized piperidine derivatives bearing unconventional substitution patterns.
(© 2011 American Chemical Society)