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

Fedor Romanov-Michailidis, Kassandra F. Sedillo, Jamie M. Neely and Tomislav Rovis*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States, Email: roviscolostate.edu

F. Romanov-Michailidis, K. F. Sedillo, J. M. Neely, T. Rovis, J. Am. Chem. Soc., 2015, 137, 8892-8895.

DOI: 10.1021/jacs.5b04946 (free Supporting Information)


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Abstract

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.

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Key Words

2,3-dihydropyridines


ID: J48-Y2015