期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 14, 期 -, 页码 593-602出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.46
关键词
asymmetric organocatalysis; Aza-Michael reaction; phase-transfer catalyst; 3-substituted isoindolinones
资金
- University Lille 1
- CNRS
- Chevreul Institute [FR 2638]
- Ministere de l'Enseignement Superieur et de la Recherche
- Region Hauts-de-France
- FEDER
A new asymmetric organocatalyzed intramolecular aza-Michael reaction by means of both a chiral auxiliary and a catalyst for stereocontrol is reported for the synthesis of optically active isoindolinones. A selected cinchoninium salt was used as phasetransfer 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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