Rhodium-Catalyzed Synthesis of Trifluoromethyl-Containing Allylic Alcohols Via <i>Z</i>-Alkenyl Transfer with High Stereochemistry Retention
Liang Cheng, Zheng‐Qiang Liu, Min Lin, Xuemei Huang, Si-Qi Xiong, Xue Zhang, Qinghua Li, Tang‐Lin Liu
Abstract
Herein, we report the rhodium-catalyzed Z -alkenyl transfer from tertiary allylic alcohols to aryl trifluoromethyl ketones, which provided an efficient way of preparation of trifluoromethyl-containing Z -allylic alcohols via β- Z -alkenyl elimination. The key Z -alkenyl-rhodium species were generated with a high degree of stereochemical retention. This reaction featured a broad substrate scope and good functional tolerance and would offer a fascinating approach for the synthesis of Z -alkenes.
Topics & Concepts
ChemistryTrifluoromethylAllylic rearrangementRhodiumCatalysisWalden inversionStereochemistryMedicinal chemistryOrganic chemistryAlkylFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms