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Ruthenium‐Catalyzed One‐Pot Tandem Isomerization–Transfer Hydrogenation Reactions of γ‐Trifluoromethylated Allylic Alcohols and β‐Trifluoromethylated Enones |
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| Authors: | Vincent Bizet Xavier Pannecoucke Jean‐Luc Renaud Dominique Cahard |
| Affiliation: | 1. UMR 6014 CNRS COBRA, Université et INSA de Rouen, 76821 Mont‐Saint‐Aignan, France, Fax: (+33)‐2‐3145‐2959;2. phone (+33)‐2‐3552‐2466;3. Normandie Université, Université de Caen Basse Normandie, UMR 6507 CNRS, Laboratoire de Chimie Moléculaire et Thioorganique, 14050 Caen, France;4. Jean‐Luc Renaud, Normandie Université, Université de Caen Basse Normandie, UMR 6507 CNRS, Laboratoire de Chimie Moléculaire et Thioorganique, 14050 Caen, France;5. Dominique Cahard, UMR 6014 CNRS COBRA, Université et INSA de Rouen, 76821 Mont‐Saint‐Aignan, France, Fax: (+33)‐2‐3145‐2959 |
| Abstract: | The ruthenium–2‐propanol combination was found to transform γ‐trifluoromethylated allylic alcohols and β‐trifluoromethylated enones into the corresponding saturated alcohols in excellent yields via a one‐pot tandem process involving isomerization and transfer hydrogenation(s). High stereospecificity was demonstrated and evidence for two mechanistic pathways is provided. The method was applied to a rapid synthesis of trifluoromethylated citronellol. |
| Keywords: | allylic compounds enones fluorine isomerization ruthenium |