Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte |
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Authors: | Maekawa Hirofumi Itoh Kotaro Goda Satoshi Nishiguchi Ikuzo |
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Institution: | Department of Chemistry, Nagaoka University of Technology, Nagaoka, Niigata, Japan. |
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Abstract: | Anodic oxidation of 1-acetoxy-3,4-dihydronaphthalene (1) and alpha-acetoxy-beta-alkylstyrenes (3) at -78 degrees C in a mixed solvent of acetonitrile (CH(3)CN), tetrahydrofuran (THF), and acetic acid (AcOH) containing (S)-tetraethylammonium camphorsulfonate as a chiral supporting electrolyte brought about enantioselective formation of the corresponding 2-acetoxy-1-tetralones (2) and (R)-2-acetoxy-1-phenyl-1-alkanone (4) with maximum enantiomeric excess (ee) of 44% and 21%, respectively. Introduction of a 7-methoxy group into 1 and increase in bulkiness of a beta-alkyl group in 3 resulted in improvement of enantioselectivity of the reactions. |
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