%0 Journal Article %T 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 %+ Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA) %+ VFP Therapies Drugs : Highway to the Brain %A Tîntas, Mihaela-Liliana %A Azzouz, R. %A Peauger, L. %A Gembus, Vincent %A Petit, Emilie %A Bailly, Laëtitia %A Papamicaël, Cyril %A Levacher, Vincent %< avec comité de lecture %@ 0022-3263 %J Journal of Organic Chemistry %I American Chemical Society %V 83 %N 17 %P 10231-10240 %8 2018 %D 2018 %R 10.1021/acs.joc.8b01442 %Z Chemical SciencesJournal articles %X 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. %G English %L hal-02024535 %U https://normandie-univ.hal.science/hal-02024535 %~ CNRS %~ INSA-ROUEN %~ COMUE-NORMANDIE %~ INC-CNRS %~ UNIROUEN %~ ENSICAEN %~ UNILEHAVRE %~ UNICAEN %~ COBRA %~ INSA-GROUPE %~ TEST-HALCNRS %~ LABOS-SYNORG