3-Menthoxybiphenyl-4-carboxylic acid: a versatile resolving agent and reagent for determination of the absolute configuration of benzylic alcohols |
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| Authors: | Shunsuke Kuwahara Nobuyoshi Tasaki Yuri Suzuki Mizuki Nakagawa Mari Ikeda Yoichi Habata |
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| Affiliation: | 1. Department of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan;2. Research Center for Materials with Integrated Properties, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan;3. Education Center, Faculty of Engineering, Chiba Institute of Technology, 2-1-1 Shibazono, Narashino, Chiba 275-0023, Japan |
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| Abstract: | A versatile reagent for the chiral resolution and determination of the absolute configuration of benzylic alcohols, (?)-3-menthoxybiphenyl-4-carboxylic acid, is reported. (?)-3-menthoxybiphenyl-4-carboxylic acid was condensed with racemic benzylic alcohols to yield diastereomeric 3-menthoxybiphenyl-4-carboxylic esters, which were separated by reversed-phase HPLC. The absolute configurations of the 3-menthoxybiphenyl-4-carboxylic esters were unambiguously determined by exciton-coupled circular dichroism. Hydrolysis of the 3-menthoxybiphenyl-4-carboxylic esters yielded enantiopure alcohols, and their absolute configurations were simultaneously determined. |
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| Keywords: | Corresponding author. |
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