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

ArticleinOrganic Letters 13(19):5152-5 · September 2011with60 Reads
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.
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