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

J Am Chem Soc. 2013 Jan 9;135(1):66-9. doi: 10.1021/ja3104389. Epub 2012 Dec 18.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Esters / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Oximes / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Esters
  • Organometallic Compounds
  • Oximes
  • Pyridines
  • Rhodium