Journal
ORGANIC LETTERS
Volume 20, Issue 13, Pages 3853-3857Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01440
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Funding
- TSRI
- Pfizer, Inc.
- National Institutes of Health [1R35GM125052]
- Bristol-Myers Squibb
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM125052] Funding Source: NIH RePORTER
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A palladium(II)-catalyzed beta,gamma-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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