Tuning the Reactivity of Difluoromethyl Sulfoximines from Electrophilic to Nucleophilic: Stereoselective Nucleophilic Difluoromethylation of Aryl Ketones

A stereoselective synthesis of enantiomerically enriched
difluoromethyl
tertiary alcohols by tuning the reactivity of difluoromethyl sulfoximines
from electrophilic to nucleophilic difluoromethylating agents is reported.
The key feature of this chemistry is the diastereoselective addition
of the difluoromethyl sulfoximine to the prochiral carbon of the ketone.
The present method was used to prepare enantiomerically enriched difluoromethyl
secondary alcohols and difluorinated analogues of the natural products
gossonorol and boivinian B, demonstrating the potency of the method.