Synthesis of cinchonidinium salts containing sulfonamide functionalities and their catalytic activity in asymmetric alkylation reactions |
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Authors: | Shinichi Itsuno Shunya YamamotoShohei Takata |
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Affiliation: | Department of Environmental & Life Sciences, Toyohashi University of Technology, Toyohashi 441-8580, Japan |
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Abstract: | Various kinds of 4-(bromomethyl)benzenesulfonamides were prepared as quaternization reagent of cinchonidine. Cinchonidinium salts obtained from the quaternization of cinchonidine with 4-(bromomethyl)benzenesulfonamide showed highly enantioselective catalytic activity in the asymmetric benzylation of N-(diphenylmethylene)glycine tert-butyl ester. The corresponding phenylalanine derivative was obtained in high yield with a high level of enantioselectivity, up to 98% ee. |
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Keywords: | Cinchonidinium salt Organocatalyst Sulfonamide Asymmetric alkylation |
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