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.
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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.
Published: 14 November 2018 by MDPI in The 22nd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: Aza-Michael reaction, phase-transfer catalyst, asymmetric organocatalysis, 3-substituted isoindolinones