Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation

Abstract

Using an iridium catalyst modified by PhanePhos, CF₃-allenes react with methanol to form branched products of hydrohydroxymethylation as single regioisomers with excellent levels of enantiomeric enrichment. This hydrogen autotransfer process enables catalytic enantioselective formation of acyclic CF₃-bearing all-carbon quaternary stereocenters in the absence of stoichiometric metals or byproducts.