Enantioselective electrophilic trifluoromethylation of beta-keto esters with Umemoto reagents induced by chiral nonracemic guanidines

Chiral nonracemic guanidines act as Bronsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of beta-keto esters by means of S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate (Umemoto reagent) with good enantioselectivity of 60-70% range. Despite the fact that the ees are still improvable, the model reported in this work could spark the imagination of chemists to design new chiral bases to improve the stereochemical outcome.