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■ Regioselective Synthesis of 4-Alkylpyridines from Pyridine and Aldehydes via Dipole Reversal Process of 1,4-Dihydropyridine Phosphonate

Phil Ho Lee,* Kooyeon Lee, Jun Hwan Shim, Seong Guk Lee, and Sundae Kim

*Department of Chemistry, Kangwon National University, Chuncheon, Kangwon 200-701, Korea

Abstract

4-Alkylation of pyridine has been accomplished by the reaction of ylides, derivated from 1,4-dihydropyridine phosphonate via phosphonioalkoxycarbonylation of pyridine with aldehydes and subsequent elimination of diisopropyl phosphate followed by aromatization with potassium tert-butoxide.