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Synthesis of 2,3-dihydropyridines

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α,β-Unsaturated oxime pivalates undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, an irreversible migratory insertion followed by reductive elimination gives 2,3-dihydropyridines in good yields. A subsequent catalytic hydrogenation can then provide piperidines.
F. Romanov-Michailidis, K. F. Sedillo, J. M. Neely, T. Rovis, J. Am. Chem. Soc., 2015, 137, 8892-8895.