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Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and ?,?-unsaturated oxime esters.

ABSTRACT: ?,?-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.

SUBMITTER: Neely JM

PROVIDER: S-EPMC3541442 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.

Neely Jamie M JM Rovis Tomislav T

Journal of the American Chemical Society 20121218 1

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. ...[more]

PMID: 23244023

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