Organocatalytic Trifluoromethylations

Significance

The research group of Shibata has developed a protocol for the efficient trifluoro­methylation of Morita-Baylis-Hillman adducts using the Ruppert-Prakash reagent (Me₃SiCF₃). The reaction proceeds through an addition-elimination-addition-elimination sequence or S_N′/S_N′ mechanism. Racemic products were obtained in good to excellent yields using DABCO (1) as catalyst. An enantioselective version of the reaction was achieved using (DHQD)₂PHAL (2) as the catalyst, which gave good to excellent enantioselectivities, albeit in lower yields than in the racemic reaction.