Ruthenium-catalyzed redox isomerization of trifluoromethylated allylic alcohols: mechanistic evidence for an enantiospecific pathway.

Vincent Bizet (1) , Xavier Pannecoucke (1) , Jean-Luc Renaud (2) , Dominique Cahard (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 LCMT - Laboratoire de chimie moléculaire et thioorganique

Transfer news : A synthetic approach to chiral β‐CF3‐substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF3‐bearing allylic alcohols by an intramolecular suprafacial enantiospecific 1,3‐hydrogen transfer (see scheme). This method was used for the enantioselective synthesis of (S )‐CF3‐citronellol.

Domaines: Chimie organique

Vincent Bizet, Xavier Pannecoucke, Jean-Luc Renaud, Dominique Cahard. Ruthenium-catalyzed redox isomerization of trifluoromethylated allylic alcohols: mechanistic evidence for an enantiospecific pathway.. Angewandte Chemie International Edition, 2012, 51 (26), pp.6467-6470. ⟨10.1002/anie.201200827⟩. ⟨hal-00996590⟩