Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System

A palladium­(II)-catalyzed β,γ-aminohydroxylation reaction of nonconjugated alkenyl carbonyl compounds has been developed. This reaction utilizes a cleavable bidentate directing group to achieve regioselective aminopalladation. The resulting chelation-stabilized alkylpalladium­(II) intermediate is then hydroxylated using oxygen/2,6-dimethyl­benzoquinone in HFIP as the mild oxidation system. Under the optimized conditions, various nucleophiles and alkene substrates are capable of delivering good yields and high diastereoselectivities of the aminohydroxylated products.