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

Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Organic Letters (Impact Factor: 6.36). 09/2011; 13(19):5152-5. 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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