Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst.
摘要：
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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关键词：
indole derivatives, isoindole derivatives C‐C bond formation organocatalysis diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism
DOI：
10.1039/b918644a
被引量：
年份：
2009
Wiley
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Wiley
万方医学
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222.252.30.203:8888
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