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Issue 67, 2020
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Synthesis of amino-diamondoid pharmacophores via photocatalytic C–H aminoalkylation

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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.

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

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Article information


Submitted
22 Apr 2020
Accepted
15 Jul 2020
First published
16 Jul 2020

Chem. Commun., 2020,56, 9699-9702
Article type
Communication

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

W. K. Weigel, H. T. Dang, H. Yang and D. B. C. Martin, Chem. Commun., 2020, 56, 9699
DOI: 10.1039/D0CC02804E

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