ChemInform Abstract: Synthesis of Perfluoroalkyl‐Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation.

Abstract

Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of EnhancedNeighboring Group Participation. -A simple, high yielding, two-step, one-pot protocol for the preparation of trifluoromethyl-substituted vinylcyclopropanes from -CF 3 homoallyl alcohols is disclosed. Destabilization of the cationic intermediate by the electron-withdrawing CF 3 group greatly enhances neighboring group participation of the alkene, allowing ring closure to predominate. The reaction can be extended to the difluoromethyl and pentafluoroethyl group, enabling the preparation of a diverse array of fluoroalkyl-substituted vinylcyclopropanes. -(KELLY, C. B.; MERCADANTE, M. A.; CARNAGHAN, E. R.; DOHERTY, M. J.; FAGER, D. C.; HAUCK, J. J.; MACINNIS, A. E.; TILLEY, L. J.; LEADBEATER*, N. E.; Eur. J. Org. Chem. 2015, 19, 4071-4076, http://dx.