Recent advances in enantioselective trifluoromethylation reactions

Recent advances in the trifluoromethylation methodology and new CF3-containing drugs

“…In the case of chiral or prochiral substrates, an underlying issue is the stereochemical control of the reaction, which can be addressed in a diastereo-or enantioselective fashion, respectively [49].…”

New β-amino-α-trifluoromethyl alcohols and their exploration in the synthesis of trifluoromethylated imidazole derivatives

“…They were obtained by treatment of arylglyoxal hydrates 5a,b with O-methyl hydroxylamine hydrochloride in the presence of sodium acetate. The subsequent nucleophilic trifluoromethylation was carried out under typical conditions using an equimolar amount of CF 3 SiMe 3 (Ruppert-Prakash reagent [8]) in dimethoxyethane (DME) in the presence of catalytic amounts of CsF.…”

“…The goal of present study was the elaboration of a method for the preparation of amino alcohols of type 2 with a primary amino group (R = H) via nucleophilic trifluoromethylation [8] of properly selected arylglyoxalimines. Furthermore, the obtained β-amino-α-trifluoromethyl alcohols should be used as starting materials for the synthesis of new imidazole N-oxides 3, bearing a β-hydroxy-β-trifluoromethyl substituent at N(1).…”

Trifluoromethylation of Carbonyl Compounds

“…Significant progress has been made in the development of asymmetric trifluoromethylation reactions [56][57][58][59][60][61][62]. However, the direct enantioselective trifluoromethylation reaction remains a challenge as recently observed when chiral crown ethers were used to the enantioselective trifluoromethylation of aldehydes and ketones [62].…”