Johnson T, Lautens M * University of Toronto, Canada
Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines.
Org. Lett. 2013;
15: 4043-4045
Key words
α-(trifluoromethyl)arylmethylamines - enantioselective synthesis - boronic acids - palladium
Significance
Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium catalysis to generate a variety of R-(trifluoromethyl)arylmethylamines with good to high enantioselectivity and yield.
Comment
The reported protocol is very versatile since it proceeds without the exclusion of ambient air and moisture. Moreover, several functional groups are tolerated, and readily available
N,O-acetals synthesized from trifluoroaldehyde are used as starting materials.
