Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 1, Pages 77-82Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b918644a
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Funding
- Natural Science Foundation [NSFC 20702052, 20902091]
- MOST [2008CB617501, 2009ZX09501018]
- Chinese Academy of Sciences
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The current article reports an organocatalytic strategy for the asymmetric catalysis of chiral oxindoles bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted oxindoles to terminal alkenes have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of Michael donor compounds (different substituted 3-aryl or methyl oxindoles), and Michael acceptor compounds (vinyl ketones and vinyl sulfones) to give the desired oxindole products with moderate to excellent yields (up to 99%) and moderate to excellent enantioselectivities (up to 91% ee).
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