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

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Chemistry Catalysis Oxime Cationic polymerization Reductive elimination Migratory insertion Medicinal chemistry Dihydropyridine Molecule Combinatorial chemistry Stereochemistry Organic chemistry Calcium

Fedor Romanov‐Michailidis , Kassandra Sedillo , Jamie M. Neely , Tomislav Rovis ·

YOU? · · 2015 · Open Access · · DOI: https://doi.org/10.1021/jacs.5b04946 · OA: W2257696768

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp(2))-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.