title: Palladium(II)-catalyzed enantioselective synthesis of α-(trifluoromethyl)arylmethylamines.
abstract: Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of α-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
authors.forename: Thomas
authors.initials: T
authors.lastname: Johnson
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D002384:Catalysis; D008024:Ligands; D008744:Methylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D008024:Ligands; D008744:Methylamines; D010080:Oxazoles; D011725:Pyridines; C064210:oxazolidine; D010165:Palladium