Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Beilstein Journal of Organic Chemistry Année : 2018

Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

Résumé

A new asymmetric organocatalyzed intramolecular aza-Michael reaction under a double auxiliary and catalyst stereocontrol is reported for the synthesis of optically active isoindolinones. A selected cinchoninium salt was used as phase-transfer catalyst in combination with a chiral nucleophile, a Michael acceptor and a base to provide 3-substituted isoindolinones in good yields and diastereomeric excesses. This methodology was applied to the asymmetric synthesis of a new pazinaclone analogue which is of interest in the field of benzodiazepine-receptor agonists. 2 Keywords Aza-Michael reaction, phase-transfer catalyst, asymmetric organocatalysis, 3-substituted isoindolinones
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Dates et versions

hal-01786976 , version 1 (31-08-2020)
hal-01786976 , version 2 (01-12-2023)

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Romain Sallio, Stéphane Lebrun, Frédéric Capet, Francine Agbossou-Niedercorn, Christophe Michon, et al.. Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue. Beilstein Journal of Organic Chemistry, 2018, 14, pp.593-602. ⟨10.3762/bjoc.14.46⟩. ⟨hal-01786976v2⟩
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