ol8b01440_si_003.zip (7.44 MB)
Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System
datasetposted on 2018-06-10, 14:14 authored by Tian Zeng, Zhen Liu, Michael A. Schmidt, Martin D. Eastgate, Keary M. Engle
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.
cleavable bidentateMild Oxidation SystemyieldAlkenediastereoselectivitieHFIPAminohydroxylationPalladiumoxidation systemalkylpalladiumalkene substratesaminohydroxylated productsregioselective aminopalladationaminohydroxylationpalladiumnucleophilechelation-stabilizednonconjugated alkenyl carbonyl compoundsoptimized conditionsIntermolecular