Chiral Hypervalent Iodine Catalysis Enables an Unusual Regiodivergent Intermolecular Olefin Aminooxygenation

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.

Automated summary

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.