期刊
TETRAHEDRON
卷 75, 期 25, 页码 3530-3542出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.05.022
关键词
Organocatalysis; Asymmetric vinylogous michael addition; Chalcones; Green synthesis; Bio-based solvent; Antiplasmodial activity
资金
- FAPESP [2013/07600-3, 2017/26679-0, 2014/50249-8]
- Serrapilheira Institute [Serra-1708-16250]
- GlaxoSmithKline
- CAPES [001]
- CNPq [405330/2016-2]
The organocatalysed asymmetric vinylogous Michael addition of alpha,alpha-dicyanoolefins to alpha,beta-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of alpha,alpha-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity. (C) 2019 Elsevier Ltd. All rights reserved.
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