Issue 88, 2016, Issue in Progress

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

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

Supplementary files

Article information

Article type
Communication
Submitted
24 Aug 2016
Accepted
29 Aug 2016
First published
30 Aug 2016

RSC Adv., 2016,6, 85058-85062

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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