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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http://dx.doi.org/10.1021/jacsau.1c00103 | DOI Listing |
J Org Chem
November 2024
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
We report a new method to create enantioenriched azatricycles using chiral α-amino acids in a two-step process after an Ugi reaction. Amino acids are great building blocks for making pure chiral molecules. Using chiral natural molecules in multicomponent reactions (MCRs) helps increase their variety by adding new chiral centers.
View Article and Find Full Text PDFOrg Lett
October 2024
Department of Chemistry, Graduate School of Science and Soft Molecular Activation Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
An oxidative remote aryl rearrangement of -cinnamyl--alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization of the alkoxybenzene ring on the benzyl group, which acts as a good aryl donor, inducing the regioselective installation of the aryl group and the oxygen atom via cascade transformation. An enantioselective oxidative remote aryl rearrangement using C2-symmetrical chiral iodoarene gave enantioenriched products with high enantioselectivity.
View Article and Find Full Text PDFChem Rev
October 2024
Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors.
View Article and Find Full Text PDFOrg Lett
August 2024
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Adv Mater
September 2024
School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.
Hypervalent iodine(III) have widely been utilized for organic synthetic reagents. They are also recognized as positive charge-assisted, exceptionally robust biaxial halogen bond donors, while their potential in supramolecular materials is barely explored. This work reports a cyclic diaryliodonium ion as biaxial halogen bonding donor that displays remarkable binding affinity toward phenanthroline or acridine acceptors with chiral pendants.
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