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

Autor: Neely JM; Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States., Rovis T
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2013 Jan 09; Vol. 135 (1), pp. 66-9. Date of Electronic Publication: 2012 Dec 18.
DOI: 10.1021/ja3104389
Abstrakt: 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.
Databáze: MEDLINE