Diastereo- and enantioselective conjugate addition of 3-substituted oxindoles to enones via bifunctional catalysts |
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| Authors: | Bin Wang Keshu Wu Pengcheng Chen Kun Liu |
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| Institution: | Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China |
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| Abstract: | This paper presents a synthetically challenging vicinal quaternary-tertiary C–C forming reaction of 3-substituted oxindoles and chalcones by a simple aryl substituted bifunctional thiourea catalyst. The reactions work with a broad range of chalcones, giving chiral 3,3′-substituted oxindoles type compounds with adjacent quaternary-tertiary stereocenters in high yields (up to 99%), very good dr (up to >98:2) and very good ee (up to 96%). |
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| Keywords: | Hydrogen-bonding catalysis Michael addition reaction Chiral thiourea Oxindole |
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