H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters |
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Authors: | Patryk Niedbaa Maciej Majdecki Piotr Grodek Janusz Jurczak |
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Institution: | Institute of Organic Chemistry PAS, 01-224 Warsaw, Poland; (P.N.); (M.M.); (P.G.) |
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Abstract: | In this work, we would like to present the development of a highly optimized method for generating the quaternary stereogenic centers in β-keto esters. This enantioselective phase-transfer alkylation catalyzed by hybrid Cinchona catalysts allows for the efficient generation of the optically active products with excellent enantioselectivity, using only 1 mol% of the catalyst. The vast majority of phase-transfer catalysts in asymmetric synthesis work by creating ionic pairs with the nucleophile-attacking anionic substrate. Therefore, it is a sensible approach to search for new methodologies capable of introducing functional groups into the precursor’s structure, maintaining high yields and enantiomeric purity. |
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Keywords: | phase-transfer catalysis organocatalysis enantioselectivity Cinchona catalysts alkylation |
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