Oxa-Diels-Alder Reaction of Isatins and Acyclic alpha,beta-Unsaturated Methyl Ketones through Cooperative Dienamine and Metal Lewis Acid Catalysis

SYNTHESIS-STUTTGART(2014)

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摘要
Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels-Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58-86%), moderate stereoselectivities (1.3:1-5.9: 1 dr, 50-81% ee), and excellent chemoselectivity.
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关键词
bifunctional catalysis,tandem reactions,Yb(OTf)(3),oxa-Diels-Alder reaction,spirooxindoles,tetrahydropyranones
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