Copper-Catalyzed Perkin-Acyl-Mannich Reaction of Acetic Anhydride with Pyridine: Expeditious Entry to Unconventional Piperidines

ArticleinOrganic Letters 13(19):5152-5 · September 2011with57 Reads
Impact Factor: 6.36 · DOI: 10.1021/ol202027k · Source: PubMed


    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.