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- Title
Enantioselective Construction of Cyclic Enaminone-Based 3-Substituted 3-Amino-2-oxindole Scaffolds via Catalytic Asymmetric Additions of Isatin-Derived Imines.
- Authors
Zhou, Lu ‐ Jia; Zhang, Yu ‐ Chen; Jiang, Fei; He, Guofeng; Yan, Jingjing; Lu, Han; Zhang, Shu; Shi, Feng
- Abstract
The first catalytic asymmetric construction of the cyclic enaminone-based 3-substituted 3-amino-2-oxindole scaffold with potential bioactivity has been developed via chiral phosphoric acid-catalyzed enantioselective addition reactions of cyclic enaminones to isatin-derived imines, which afforded a series of cyclic enaminone-based 3-substituted 3-amino-2-oxindoles in high yields and excellent enantioselectivities (up to 99% yield, 97% ee). The investigation of the reaction mechanism suggested that it was facilitated by a dual hydrogen-bonding activation mode between the two substrates and the chiral phosphoric acid. Besides, this method could be utilized for a large-scale synthesis with maintained enantioselectivity. This approach will not only offer a useful method for enantioselective construction of the cyclic enaminone-based 3-substituted 3-amino-2-oxindole scaffold, but also enrich the research on catalytic asymmetric addition reactions of isatin-derived imines by using electron-rich olefins as nucleophiles. More importantly, a preliminary evaluation on the cytotoxicity of some selected products revealed that two of the enantio-pure compounds exhibited moderate to strong cytotoxicity to A549, 786-0, ECA109 and BT474 cancer cell lines.
- Subjects
ENANTIOSELECTIVE catalysis; ENAMINES; PHOSPHORIC acid; ISATIN; IMINES; ANTINEOPLASTIC agents
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 19, p3069
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600508