Dauben-Michno oxidative transposition of allylic cyanohydrins - Enantiomeric switch of (-)-carvone to (+)-carvone

Abstract

Allylic cyanohydrins were subjected to Dauben-Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (-)-carvone to its enantiomer. © 2011 Published by NRC Research Press.