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Rh(III)-Catalyzed Regioselective Synthesis of Pyridines from Alkenes and α,β-Unsaturated Oxime Esters

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journal contribution
posted on 09.01.2013, 00:00 by Jamie M. Neely, Tomislav Rovis
α,β-Unsaturated O-pivaloyl oximes are coupled to alkenes by Rh­(III) catalysis to afford substituted pyridines. The reaction with activated alkenes is exceptionally regioselective and high-yielding. Mechanistic studies suggest that heterocycle formation proceeds via reversible C–H activation, alkene insertion, and a C–N bond formation/N–O bond cleavage process.