Synthesis of novel chiral 1,3-aminophenols and application for the enantioselective addition of diethylzinc to aldehydes |
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Affiliation: | 1. Department of Applied Chemistry, Faculty of Engineering, Saitama University, 255 Shimo-ohkubo, Sakura, Saitama 338-8570, Japan;2. Department of Chemical Engineering, University of Jinan, 106 Jiwei Road, Jinan, Shandong Province 250022, China |
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Abstract: | Novel chiral 1,3-aminophenols were efficiently synthesized by applying a Friedel–Crafts reaction and optical resolution. The catalytic activity of the aminophenols was studied for the addition of diethylzinc to benzaldehyde. The results showed that (S)-5a with bulky tert-butyl groups on the stereogenic carbon atom and 4,6-positions of phenol favored higher enantioselectivity (94% ee). The same ligand was also used with other aldehydes, to give optically active alcohols in good chemical yields and ee values (up to 99%). |
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