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

Abstract

Chiral nonracemic guanidines act as Brønsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of β-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.