Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System
Tian Zeng1, Zhen Liu1, Michael A Schmidt2
1Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Abstract:
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.
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