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.
J Org Chem
; 83(17): 10231-10240, 2018 09 07.
Article
em En
| MEDLINE
| ID: mdl-30004228
ABSTRACT
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 ß-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 99.50.5; 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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Di-Hidropiridinas
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Pró-Fármacos
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Doença de Alzheimer
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Donepezila
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article