Amine-Catalyzed Tandem Reactions of Morita–Baylis–Hillman Acetates with Isatins: Facile Synthesis of 3-Hydroxyoxindoles
European Journal of Organic Chemistry(2017)
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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