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Dauben–Michno oxidative transposition of allylic cyanohydrins — Enantiomeric switch of (–)-carvone to (+)-carvone*Based on the 2010 Bader Award Lecture.
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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.
Canadian Science Publishing
Title: Dauben–Michno oxidative transposition of allylic cyanohydrins — Enantiomeric switch of (–)-carvone to (+)-carvone*Based on the 2010 Bader Award Lecture.
Description:
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.
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