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Issue 88, 2016, Issue in Progress
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Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

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Abstract

The synthesis of fluorinated donepezil, a promising new therapeutic agent for Alzheimer's disease, was achieved by the palladium-catalyzed decarboxylative allylation (DcA) of an allylic ester having a tri-substituted heterocyclic alkene system as a key step. This strategy is very different from a patented method for the title compound which was successfully extended to the first catalytic asymmetric synthesis of fluorinated donepezil. Fluorinated donepezil showed a noticeable magnitude in the self-disproportionation of enantiomers.

Graphical abstract: Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

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Publication details

The article was received on 24 Aug 2016, accepted on 29 Aug 2016 and first published on 30 Aug 2016


Article type: Communication
DOI: 10.1039/C6RA21253K
RSC Adv., 2016,6, 85058-85062

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    Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of α-fluoro-β-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

    M. Maeno, H. Kondo, E. Tokunaga and N. Shibata, RSC Adv., 2016, 6, 85058
    DOI: 10.1039/C6RA21253K

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