An economic,practical access to enantiopure 1,1′-bi-2-naphthols: enantioselective complexation of threo-(1S,2S)-N-benzyl-N,N-dimethyl[1,3-dihydroxy-1-(4′-nitrophenyl)]-2-propylammonium chloride |
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| Institution: | 1. Department of Chemistry, School of Arts and Sciences, The Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, United States;2. W. Harry Feinstone Department of Molecular Microbiology and Immunology, Bloomberg School of Public Health, The Johns Hopkins University, Baltimore, MD 21205, United States;3. The Johns Hopkins Malaria Research Institute, Bloomberg School of Public Health, The Johns Hopkins University, Baltimore, MD 21205, United States;1. Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan;2. Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan;1. Medicinal Chemistry Department, A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Lustdorfska dor. 86, Odessa, Ukraine;2. Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznan, Poland;3. Institute of Applied Physics, Academy of Sciences of Moldova, Chisinau, Republic of Moldova;1. National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine;2. Enamine Ltd, Alexandra Matrosova Street 23, Kyiv 01103, Ukraine;3. STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Lenina ave. 60, 61001 Kharkiv, Ukraine;1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China;2. College of Life Science, Sichuan University, Chengdu 610064, PR China;3. Wenzhou University, Wenzhou 325035, PR China |
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| Abstract: | An economic, convenient access to enantiopure (R)- and (S)-1,1′-bi-2-naphthol (BINOL) has been discovered. Racemic 1,1′-bi-2-naphthol was reacted with threo-(1S,2S)-N-benzyl-N,N-dimethyl-1,3-dihydroxyl-1-(4′-nitrophenyl)]-2-propylammonium chloride (BDDNPAC) in water-containing acetonitrile under reflux until the solid dissolved completely, and then cooled to ambient temperature to isolate a yellow-greenish crystal consisting of BDDNPAC, (S)-BINOL, and water, which was analyzed by single crystal X-ray structural analysis. Enantiopure (S)- and (R)-1,1′-bi-2-naphthols were obtained in high yield after decomposition of the colored crystalline complex and evaporation of the acetonitrile solution removed from the complex crystals and successive crystallization. The chiral quaternary ammonium salt BDDNPAC can be recovered and reused without any decrease in efficiency. |
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