Chiral bifunctional thiourea-catalyzed enantioselective aldol reaction of trifluoroacetaldehyde hemiacetal with aromatic ketones

In the presence of saccharide-derived bifunctional amine-thiourea catalysts, the direct aldol condensation of trifluoroacetaldehyde methyl hemiacetal with aromatic ketones proceeds to produce (R)-β-hydroxy β-trifluoroalkyl ketones in low to moderate yields with good enantioselectivities.

Graphical abstract(R)-β-hydroxy β-trifluoroalkyl ketones were prepared through enantioselective thiourea-catalyzed aldol condensation of trifluoroacetaldehyde methyl hemiacetal with aromatic ketones.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► An enantioselective aldol reaction of CF3CH(OH)OMe with ketones is described. ► Chiral bifunctional amine-thiourea catalysts was used. ► Optically active (R)-β-hydroxy β-trifluoroalkyl ketones were obtained.