Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles via Morita−Baylis−Hillman Reaction
Journal of the American Chemical Society2010Vol. 132(43), pp. 15176–15178
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Abstract
We report a highly enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins and acrolein to provide enantiomerically enriched 3-substituted 3-hydroxyoxindoles, which could serve as valuable synthetic building blocks. This is also the first time that a ketone has been used as the electrophile and acrolein as the nucleophile in a highly enantioselective catalytic asymmetric MBH reaction. Hatakeyama's catalyst, β-isocupreidine (1), turned out to be a powerful catalyst for this transformation.
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