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

ABSTRACT: A palladium(II)-catalyzed ?,?-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.

SUBMITTER: Zeng T

PROVIDER: S-EPMC6039249 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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

Zeng Tian T Liu Zhen Z Schmidt Michael A MA Eastgate Martin D MD Engle Keary M KM

Organic letters 20180611 13

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 yie ...[more]

PMID: 29888604

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