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Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation

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journal contribution
posted on 22.07.2015, 00:00 authored by Fedor Romanov-Michailidis, Kassandra F. Sedillo, Jamie M. Neely, Tomislav Rovis
α,β-Unsaturated oxime pivalates are proposed to undergo reversible C­(sp2)–H insertion with cationic Rh­(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

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