Condensation of N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give highly diastereomerically enriched adducts 5a-g. Acidic methanolysis of 5a-g provided the desired 1-aryl-2,2,2-trifluoroethylamine hydrochloride compounds 6a-g. [reaction: see text].
Amines Q 0120Asymmetric Syntheses of 1-Aryl-2,2,2-trifluoroethylamines via Diastereoselective 1,2-Addition of Arylmetals to 2-Methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide. -Imine (III), generated in situ, is used without isolation and purification in the reaction with various aryllithium reagents. Acidic methanolysis of the products provides the desired target compounds. -(TRUONG*, V. L.; MENARD, M. S.; DION, I.; Org. Lett. 9 (2007) 4, 683-685; Dep. Med. Chem., Merck Frosst Cent. Ther. Res., Kirkland, Que. H9H 3L1, Can.; Eng.) -R. Steudel 26-060
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