Access to Highly Enantioenriched Donepezil-like 1,4-Dihydropyridines as Promising Anti-Alzheimer Prodrug Candidates via Enantioselective Tsuji Allylation and Organocatalytic Aza-Ene-Type Domino Reactions

This work aims at exploiting both the enantioselective Tsuji allylation of allyl carbonate 6 and an organocatalytic aza-ene-type domino reaction between enal 3a and β-enaminone 4a to develop a straightforward access to all of the four possible stereoisomers of a donepezil-like 1,4-dihydropyridine 1a...

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Published in:Journal of organic chemistry 2018-09, Vol.83 (17), p.10231-10240
Main Authors: Ţînţaş, Mihaela-Liliana, Azzouz, Rabah, Peauger, Ludovic, Gembus, Vincent, Petit, Emilie, Bailly, Laetitia, Papamicaël, Cyril, Levacher, Vincent
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Organic chemistry
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cited_by cdi_FETCH-LOGICAL-a408t-284c692303ce4342484821e428be0599a9e2a3165969d206393c1357eb452b023
cites cdi_FETCH-LOGICAL-a408t-284c692303ce4342484821e428be0599a9e2a3165969d206393c1357eb452b023
container_end_page 10240
container_issue 17
container_start_page 10231
container_title Journal of organic chemistry
container_volume 83
creator Ţînţaş, Mihaela-Liliana
Azzouz, Rabah
Peauger, Ludovic
Gembus, Vincent
Petit, Emilie
Bailly, Laetitia
Papamicaël, Cyril
Levacher, Vincent
description This work aims at exploiting both the enantioselective Tsuji allylation of allyl carbonate 6 and an organocatalytic aza-ene-type domino reaction between enal 3a and β-enaminone 4a to develop a straightforward access to all of the four possible stereoisomers of a donepezil-like 1,4-dihydropyridine 1a (er up to 99.5:0.5; overall yield up 64%), an anti-Alzheimer’s prodrug candidate. This strategy was extended to the preparation of other enantioenriched 1,4-dihydropyridines 1b–i (eight examples), highlighting its potential in the development of these chiral AChE inhibitors.
doi_str_mv 10.1021/acs.joc.8b01442
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subjects Chemical Sciences
Organic chemistry
title Access to Highly Enantioenriched Donepezil-like 1,4-Dihydropyridines as Promising Anti-Alzheimer Prodrug Candidates via Enantioselective Tsuji Allylation and Organocatalytic Aza-Ene-Type Domino Reactions
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