Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via Morita-Baylis-Hillman reaction |
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| Authors: | Liu Yun-Lin Wang Bo-Lun Cao Jun-Jie Chen Long Zhang Yong-Xue Wang Chao Zhou Jian |
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| Institution: | Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China. |
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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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