Synthesis of C2-symmetric chiral crown ethers by lipase-catalyzed reactions |
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| Authors: | Misako NakamuraTakuya Taniguchi Naohisa IshidaKeishi Hayashi Masahiro MuraokaYohji Nakatsuji |
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| Institution: | Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, 5-16-1 Omiya, Asahi-ku, Osaka 535-8585, Japan |
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| Abstract: | Kinetic resolution of a racemic mixture of C2-symmetric 18-crown-6 diols (rac-1a) and 15-crown-5 diol (rac-1c) was achieved by lipase-catalyzed acetylation. The enantiomeric excess of the chiral crown diols (95% ee and 82% ee) was determined by 1H NMR spectroscopy, using (R)-(+)-1-(1-naphthyl)ethylammonium hydrochloride as a shift reagent. The C2-symmetric chiral 15-crown-5 diol (>95% ee) was also obtained by kinetic resolution of the racemic diacetate (rac-2c) using lipase-catalyzed solvolysis. |
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| Keywords: | Chiral crown ethers Lipase-catalyzed reaction Enantiomeric excess Absolute configuration |
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