Synthesis of amino-diamondoid pharmacophores photocatalytic C-H aminoalkylation

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 v...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-08, Vol.56 (67), p.9699-972
Main Authors: Weigel, William K, Dang, Hoang T, Yang, Hai-Bin, Martin, David B. C
Format: Article
Language:English
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Summary: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. 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc02804e