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

作者：Hudlicky Jason R; Werner Lukas; Semak Vladislav; Simionescu Razvan; Hudlicky Tomas^*

来源：Canadian Journal of Chemistry, 2011, 89(5): 535-543.

DOI：10.1139/V11-026

• Dauben-Michno reaction
• oxidative 1,3-transposition of allylic alcohols
• cyanoenones
• enantiomeric switch of carvone

Allylic cyanohydrins were subjected to Dauben-Michno oxidation at low temperatures to provide beta-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.

• 出版日期2011-5