Resolution of (±)-[2.2]paracyclophane-4,12-dicarboxylic acid |
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| Institution: | 1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., Rostov on Don 344090, Russia;2. Southern Scientific Center of Russian Academy of Science, 41, Chekhova Str., Rostov on Don 344006, Russia;1. Miwon Commercial, 49 Wonsiro, Danwongu, Ansan, Gyeonggi-do, 15610, Republic of Korea;2. School of Integrative Engineering, Chung-Ang University, 84 Heukseok-Ro, Dongjak-gu, Seoul, 156-756, Republic of Korea;3. Department of Chemistry, Hankuk University of Foreign Studies, Yongin, 449-791, Gyeonggi-do, Republic of Korea;1. Department of Chemical Enginnering and Biotechnology, National Taipei University of Technology, Taipei 10608, Taiwan (ROC);2. Department of Biochemistry, College of Medicine, Taipei Medical University, No. 250, Wu-xing Street, Taipei 110, Taiwan (ROC) |
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| Abstract: | The resolution of (±)-2.2]paracyclophane-4,12-dicarboxylic acid (±)-1 has been realized through the diastereomeric esters of (1S)-hydroxymethyl-4,7,7-trimethyl-2-oxabicyclo-2.2.1]heptan-3-one, simply separated by flash chromatography and hydrolyzed with tBuOK/H2O. (R)-(?)-1 and (S)-(+)-1 were obtained in high enantiomeric excesses (>97%) while the determinations of the absolute configurations of (R)-1 and (S)-1 were carried out by X-ray diffraction. |
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