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Synthesis of amino-diamondoid pharmacophores via photocatalytic C–H aminoalkylation

Year: 2020
Type: article
Abstract: We report a direct C-H aminoalkylation reaction using two light-activated H-atom transfer catalyst systems that enable the introduction of protected amines to native adamantane scaffolds with C-C bond formation. The scope of adamantane and imine reaction partners is broad and deprotection provides versatile amine and amino acid building blocks. Using readily available chiral imines, the enantioselective synthesis of the saxagliptin core and rimantadine derivatives is also described.
DOI: 10.1039/d0cc02804e
Language: English
Field: Chemistry
Open Access status: green
Funders: National Science Foundation, University of Iowa, National Institutes of Health, U.S. Army, University of California, Riverside, National Center for Research Resources
Awards: Purchase of a Liquid Chromatograph-TOF Mass Spectrometer, Acquisition of a 600-MHz Nuclear Magnetic Resonance Spectrometer, G2926040067, MRI: Acquisition of an Upgrade to a Console with Solid State Capabilities for a 14.1 T Magnet, G4865018894, Acquisition of a GC-TOF Mass Spectrometer
OpenAlex ID: W3043559007
FWCI: 2.55
Cites: 64
Cited by: 40
Related to: 10