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Amine-Catalyzed Tandem Reactions of Morita–Baylis–Hillman Acetates with Isatins: Facile Synthesis of 3-Hydroxyoxindoles

European Journal of Organic Chemistry(2017)

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Abstract
An amine‐catalyzed reaction between Morita–Baylis–Hillman (MBH) acetates and isatins to provide facile access to structurally interesting 3‐hydroxyoxindoles in moderate to good yields with diastereomeric ratios of 1:1 has been developed. A wide variety of isatin derivatives were tolerated under the conditions of this tandem reaction. Notably, the inert homoallylic methyl group of MBH acetate 1 was directly involved in the bond formation step, which was followed by a [4+2] annulation under mild conditions to lead to the desired products.
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Key words
Organocatalysis,Nitrogen heterocycles,Amines,Domino reactions,Allylic compounds
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