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. 2020 Aug 20;56(67):9699-9702.
doi: 10.1039/d0cc02804e.

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

William K Weigel 3rd  1 , Hoang T Dang  1 , Hai-Bin Yang  2 , David B C Martin  1
Affiliations

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

William K Weigel 3rd et al. Chem Commun (Camb). .

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.

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Conflict of interest statement

Conflicts of interest

There are no conflicts to declare.

Figures

Figure 1.
Figure 1.
Bioactive aminoadamantanes and synthetic approaches for the preparation of aminoalkylated molecules.
Scheme 1.
Scheme 1.
Deprotection reactions with SmI2 and TFA to afford free amines.
Scheme 2.
Scheme 2.
Mechanism of PT-catalyzed aminoalkylation reaction.
See this image and copyright information in PMC

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