Journal
JACS AU
Volume 1, Issue 6, Pages 734-741Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacsau.1c00103
Keywords
Regiodivergent; Chiral Hypervalent Iodine Catalysis; Olefin Oxyamination; Iodide Catalysis; Amino Alcohol
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Funding
- National Institute of General Medical Sciences of the National Institutes of Health [R15GM139156]
- University of Toledo
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A novel iodide-catalyzed intermolecular aminooxygenation strategy is described, utilizing amide as the O- and N-source for regiocontrol. It was found that simple additives can selectively introduce regiodivergent oxyamination processes for electronically activated alkenes while being regio-complementary for unactivated alkenes. Preliminary data also suggests that this regiocontrol strategy can be applied in asymmetric processes using chiral hypervalent iodine catalysis.
A novel iodide-catalyzed intermolecular aminooxygenation strategy is described here. Amide is used as the O- and N-source to probe for regiocontrol strategies. Notably, simple additives can be selectively introduced to achieve regiodivergent oxyamination processes for electronically activated alkenes while being regio-complementary for unactivated alkenes. Our preliminary data demonstrates that this regiocontrol strategy based on nucleophile can also be applied in asymmetric processes using chiral hypervalent iodine catalysis.
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