Epimerization reaction of a substituted vinylcyclopropane catalyzed by ruthenium carbenes: mechanistic analysis.

@article{Zeng2006EpimerizationRO,
  title={Epimerization reaction of a substituted vinylcyclopropane catalyzed by ruthenium carbenes: mechanistic analysis.},
  author={Xingzhong Zeng and Xudong Wei and Vittorio Farina and Elio Napolitano and Yibo Xu and Li Zhang and Nizar Haddad and Nathan Yee and N. I. Grinberg and Sherry Y. Shen and Chris H. Senanayake},
  journal={The Journal of organic chemistry},
  year={2006},
  volume={71 23},
  pages={8864-75}
}
A novel ruthenium carbene-catalyzed epimerization of vinylcyclopropanes is reported. The reaction rate strongly depends on the presence of ruthenium ligands in solution. When the first-generation Grubbs catalyst is employed, a 5.3:1 equilibrium ratio of epimers is established quickly, but when a first-generation Hoveyda catalyst is employed, epimerization is observed only if an additional phosphine or nitrogen ligand is added. NMR and kinetic studies suggest that the isomerization reaction… CONTINUE READING

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