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High enantioselective Michael addition of malonates to β,γ-unsaturated α-ketoesters catalyzed by bifunctional thioureas
Authors:Swapna Konda  John C-G Zhao
Institution:Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0968, USA
Abstract:A highly enantioselective Michael addition of malonates to β,γ-unsaturated α-ketoesters was achieved using cinchona alkaloid-derived thioureas as the bifunctional catalyst. The corresponding Michael addition products were obtained in excellent yields (90–99%) and ee values (up to >99% ee) using a quinidine-derived thiourea as the catalyst under neat conditions. The opposite enantiomer may be obtained using a quinine- or cinchonidine-derived thiourea as the catalyst.
Keywords:Organocatalysis  Michael addition  Cinchona alkaloid thiourea  Malonate  Ketoester
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